Takata, Toshihiro et al. published their research in Bulletin of the Chemical Society of Japan in 1962 |CAS: 51566-22-4

3-Methylpyridine-2,6-diamine(cas:51566-22-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of 3-Methylpyridine-2,6-diamine

Takata, Toshihiro published an article in 1962, the title of the article was Synthesis of methylpyridine and 1,8-naphthyridine derivatives.Safety of 3-Methylpyridine-2,6-diamine And the article contains the following content:

When a mixture of 43 g. α,α’-dimethylglutaronitrile (I) and 30 g. NaNH2 in 258 ml. HCONH2 was kept for 2 days, filtered, and washed with PrOH and EtOAc, 41 g. α,α’-dimethylglutarimidine (II), m. 209-10° (decomposition) (absolute EtOH), was obtained. Similarly α-methylglutaronitrile gave 70% of α-methylglutarimidine (III), m. 154-5° (decomposition) (absolute EtOH). Reduction of 7 g. II in 100 ml. absolute EtOH was carried out with 98 g. Na and excess EtOH. Steam distillation of the product and evaporation of the acidified distillate and basification with NaOH gave 4.6 g. 3,5-dimethylpiperidine (IV), b. 144°, d20 0.8532, n20D 1.4560; picrate m. 184°. Reduction of III gave 3-methylpiperidine (V), b. 125-6°, d20 0.8570, n20D 1.4506; picrate m. 105°. Dehydrogenation of 0.5 g. IV with 0.2 g. of a Pd catalyst gave 0.35 g. 3,5-dimethylpyridine (VI), b. 168-71°, d20 0.9096, n20D 1.4501; picrate m. 242-3° (decomposition). 3-Methylpyridine (VII) was obtained similarly from V; picrate m. 149-50°. Dehydrogenation of 1 g. II in 4 ml. Ph2O at 300° for 11 hrs. with Pd catalyst gave 0.3 g. 2,6-diamino-3,5-dimethylpyridine (VIII), m. 186-7° (C6H6). VIII was acetylated with Ac2O in a sealed tube at 170° for 1 hr. to give the tetraacetyl derivative (IX), m. 149° (C6H6). Acetylation of VIII at 95° for 1 hr. gave the diacetyl derivative (X), m. 197°. 2,6-Diamino-3-methylpyridine (XI), m. 156-7°, was obtained in 30% yield by the dehydrogenation of III with Pd catalyst. Treatment of 12.2 g. VII with 16 g. NaNH2 in 16 g. Tetralin at 150-3° for 4 hrs. and at 198-200° for 17 hrs. and pouring the mixture into H2O and extraction with C6H6 and evaporation gave 2.5 g. XI. Acetylation of XI with Ac2O at 170-180° for 3 hrs. gave the triacetyl derivative, m. 142-4°. Acetylation of XI with Ac2O at 90-100° for 1 hr. gave the diacetyl derivative, m. 220-1°. Treatment of 2,4,6-tricyano-n-heptane (XII) with NaNH2 as before gave 3,6-dihydro-2,7-diiminooctahydro-1,8-naphthyridine (XIII), m. 222-4° (decomposition), in 87% yield and 1,3,5-tricyanohexane (XIV) gave 3-methyl-2,7-diiminooctahydro-1,8-naphthyridine (XV), m. 204-6° (decomposition), in 65% yield, while 1,3,5-tricyanopentane (XVI) gave 2,7-diiminooctahydro-1,8-naphthyridine (XVII) in 82% yield. A solution of 1.5 g. XIII in 240 ml. amyl alcohol was reduced with 21 g. Na at 130-40°. Working up as for IV gave 1 g. 3,6-dimethyldecahydro-1,8-naphthyridine (XVIII), m. 162-3° (C6H6); dipicrate m. 213° (decomposition). Similar reductions of 7 g. XV in 800 ml. amyl alcohol and 98 g. Na gave 4 g. 3-methyldecahydro-1,8-naphthyridine (XIX), m. 116-17° [dipicrate m. 205° (decomposition)] and of 1.2 g. XVII with 17 g. Na gave 0.9 g. decahydro-1,8-naphthyridine (XX), m. 116-17° (dipicrate m. 195°). Dehydrogenation of XVIII with a Pd catalyst in Ph2O gave 3,6-dimethyl-1,8-naphthyridine (XXI), m. 191-2° (petr. ether) in 71% yield; picrate m. 210-11° (decomposition). To a mixture of 320 g. CH2(CO2Et)2 (XXII) and 280 g. CH2:CMeCN was added a solution of 11 g. Na in 80 g. EtOH and the mixture stirred at 30-50° for 8 hrs. and at 80-90° for 2 hrs. Addition of HCl, and distillation of the product gave 338 g. α,α’-dimethyl-γ,-γ-dicarbethoxypimelonitrile (XXIII), b2 175°. γ,γ-Dicarbethoxypimeronitrile (XXIV), m. 60-2°, was obtained in 76% yield from 187 g. XXII, and 123 g. acrylonitrile and 10.6 ml. of 30% KOH in aqueous MeOH at room temperature for 2 hrs. XXIII (115 g.) was hydrolyzed with 55 g. KOH in 500 ml. absolute EtOH for a few days at room temperature Addition of water, acidification, and extraction with EtOAc gave α,α’-dimethyl-γ,γ-dicarboxypimelonitrile (XXV), m. 134-6° (decomposition). Similarly XXIV gave the corresponding diacid (XXVI), m. 158°. The K salt of XXV (47.1 g.) in 50% aqueous EtOH was treated with H at 100 atm. below 60° in the presence of 19 g. Raney Ni catalyst and the mixture was concentrated, acidified, and heated at 200° for 3 hrs. Addition of NaOEt in EtOH gave 20 g. 3-(β-methyl-ω-aminopropyl)-5-methyl-2-piperidone (XXVII); picrate m. 184-6°. Pyrolysis of 0.7 g. XXVII at 300° gave after purification as the hydrochloride and basification, 3,6-dimethyltetrahydro-1,8-naphthyridine (XXVIII), m. 110-11°; monopicrate m. 256°. Dehydrogenation of 0.11 g. XXVIII in 2 ml. Ph2O at 250-80° for 20 hrs. in the presence of Pd catalyst gave XXI. Reduction of XXVIII with Na in amyl alcohol gave XVIII. Reduction of 28 g. K salt of XXVI with Raney Ni as for XXV gave 13 g. 3-(ω-aminopropyl)-2-piperidone (XXIX); picrate m. 207°. Pyrolysis of XXIX gave hexahydro-1,8-naphthyridine; picrate m. 228-30°. The experimental process involved the reaction of 3-Methylpyridine-2,6-diamine(cas: 51566-22-4).Safety of 3-Methylpyridine-2,6-diamine

3-Methylpyridine-2,6-diamine(cas:51566-22-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Safety of 3-Methylpyridine-2,6-diamine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kolder, C. R. et al. published their research in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1953 |CAS: 861024-77-3

2,4-Dibromo-3-chloropyridine(cas:861024-77-3) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.HPLC of Formula: 861024-77-3

Kolder, C. R.; den Hertog, H. J. published an article in 1953, the title of the article was Synthesis and reactivity of 5-chloro-2,4-dihydroxypyridine.HPLC of Formula: 861024-77-3 And the article contains the following content:

The synthesis of 5-chloro-2,4-dihydroxypyridine (I) is described. 4-Nitropyridine 1-oxide (II) (24 g.), prepared by known procedures was heated 6 hrs. at 110° (sealed tube) with 120 ml. SO2Cl2, giving 7 g. 2,4-dichloropyridine (III), b1.5 73-5°, and 5.5 g. recovered II. From heating the flask residue left from vacuum distillation of III with concentrated aqueous NH3 at 180° was obtained 1.5 g. 4-amino-2,3,5-trichloropyridine, m. 147-8°. III (12 g.) heated 5 hrs. at 170-80° (sealed tube) with 150 ml. aqueous NH3, 25 g. NaOH added, and the product extracted with Et2O gave 2 g. 2-amino-4-chloropyridine, m. 130-1°, and 6 g. 4-amino-2-chloropyridine (IV), m. 91-1.5°. IV (3 g.) heated 6 hrs. at 160° (sealed tube) with a solution of 1 g. Na in 15 ml. absolute EtOH gave 2 g. (60-5%) 4-amino-2-ethoxypyridine (V), m. 88-9°. V (0.4 g.) in 20 ml. saturated HCl treated dropwise with 0.25 g. NaNO2 in H2O in the cold gave 0.4 g. (85-90%) 4-chloro-2-ethoxypyridine (VI), m. -1 to + 1°; picrate, m. 130-1°. VI chlorinated in HOAc with Cl gas gave 75-80% 4,5-dichloro-2-ethoxypyridine (VII), m. 56-7°. VII (1 g.) heated 8 hrs. at 160° (sealed tube) with 1 g. NaOH in 20 ml. 50% aqueous EtOH gave 0.6 g. 5-chloro-2,4-diethoxypyridine (VIII), m. 56.5-57°, and 0.35-0.4 g. 5-chloro-2-ethoxy-4-hydroxypyridine, m. 201.5-2°. VIII (0.65 g.) heated 4 hrs. at 160° (sealed tube) with 20 ml. 25% aqueous HCl gave 0.47 g. (95-100%) I, m. 273-4° (decomposition) VII (0.1 g.) heated 4 hrs. at 160° (sealed tube) with 3 ml. 25% aqueous HCl gave 90-100% 4,5-dichloro-2-hydroxypyridine (IX), m. 231° (decomposition). IX heated with NaOEt solution as above gave 5-chloro-4-ethoxy-2-hydroxypyridine, m. 209.5-10.5°. IX heated 2.5 hrs. at 120-30° (sealed tube) with 3.5 ml. POCl3 gave 2,4,5-trichloropyridine (X), m. 8-9°. X heated with aqueous NH3 gave 4-amino-2,5-dichloropyridine, m. 125.5-26°; picrate, m. 164-5°. I heated with POCl3 gave X; POBr3 gave 2,4-dibromo-5-chloropyridine (XI), m. 61.5-2.5°. I heated with HCl or HBr at 250° gave only unchanged starting material but when heated in 48% aqueous HBr containing Br it gave 3-bromo-5-chloro-2,4-dihydroxypyridine (XII), m. 258-9° (decomposition), no depression with an authentic specimen. XII with POCl3 gave 3-bromo-2,4,5-trichloropyridine (XIII), m. 37-7.5°, and with POBr3 2,3,4-tribromo-5-chloropyridine (XIV), m. 77.5-8.5°. Mixed m.ps. of XI with the 3-Cl somer, of XIII with 5-bromo-2,3,4-trichloropyridine, and of XIV with 2,4,5-tribromo-3-chloropyridine all gave depressions indicating non-identity and serving as further evidence of the assigned structures. The experimental process involved the reaction of 2,4-Dibromo-3-chloropyridine(cas: 861024-77-3).HPLC of Formula: 861024-77-3

2,4-Dibromo-3-chloropyridine(cas:861024-77-3) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.HPLC of Formula: 861024-77-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Talik, T. et al. published their research in Acta Poloniae Pharmaceutica in 1955 |CAS: 636-73-7

Pyridine-3-sulfonic acid(cas:636-73-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 636-73-7

Talik, T.; Plazek, E. published an article in 1955, the title of the article was Syntheses of the hydrazides of pyridinesulfonic acids.Related Products of 636-73-7 And the article contains the following content:

The hydrazides were prepared from pyridinesulfonyl chlorides and N2H4.H2O (I); synthesis of 2- and 4-pyridinesulfonyl chlorides (II and III, resp.) was described in a previous article (cf. preceding abstract). II (from 4 g. 2-mercaptopyridine) was added to 3.6 g. I in 5 mL. H2O with cooling below 30°. On further cooling, 2-pyridylsulfonylhydrazide (IV) crystallized, m. 86-7° (decomposition) (from MeCl). With acetone, IV gave the hydrazone, m. 172-4°. From a similarly treated mixture of I and III, no hydrazide could be isolated; upon addition of acetone, however, acetone 4-pyridylsulfonylhydrazone was obtained, m. 148-9° (decomposition). From 3-pyridinesulfonyl chloride (Francis, C.A. 37, 66529) and I, 3-pyridylsulfonylhydrazide (V) was prepared, m. 152-3° (decomposition) (from H2O); monopicrate, m. 120-1° (decomposition); acetone hydrazone (VI), m. 152-3° (decomposition) (from H2O), monopicrate of VI, m. 126° (decomposition). On heating with H2O or EtOH and on standing at room temperature IV decomposed into N and 2,2′-dipyridyl disulfite, m. 53°; picrate, m. 110°. The experimental process involved the reaction of Pyridine-3-sulfonic acid(cas: 636-73-7).Related Products of 636-73-7

Pyridine-3-sulfonic acid(cas:636-73-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 636-73-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

den Hertog, H. J. et al. published their research in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1945 |CAS: 861024-77-3

2,4-Dibromo-3-chloropyridine(cas:861024-77-3) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Product Details of 861024-77-3

den Hertog, H. J. published an article in 1945, the title of the article was Derivatives of pyridine and quinoline. LIX. Bromopyridines.Product Details of 861024-77-3 And the article contains the following content:

Pyridine (I) is brominated at 300° in the vapor phase and 3-bromopyridine (II) separated by distillation 3,5-Dibromopyridine (III) seps. upon cooling the residue; it is filtered off and the filtrate (400 g.) is fractionated under 20 mm. through a 20-cm. Widmer column. Fraction (1), 95° (55 g.), was II; (2), 95-100° (25 g.), was 3,4-dibromopyridine (IV) and III; (3), 100-5° (50 g.), was III, IV, and 2,5-dibromopyridine (V); (4), 105-10° (45 g.), was III, 2,3-dibromopyridine (VI), and V; (5), 110-15° (50 g.), was VI; (6), 115-20° (50 g.), was 2,6-dibromopyridine (VII); (7), 120-25° (30 g.), was VII; (8), 125-30° (20 g.), was VII and 3,4,5-tribromopyridine (VIII); (9), 130-35° (15 g.), was VII, VIII, and 2,3,5-tribromopyridine (IX); (10), 135-140° (20 g.), was VIII and IX; (11), 140-45° (25 g.), was VIII and IX; residue (15 g.). Fraction (3) (typical treatment) was shaken with 80 ml. of 8% HCl, the insoluble portion (A) separated from the soluble portion (B) which was poured into concentrated NH4OH. The crystals which separated (10 g.), recrystallized from petr. ether, yielded 5.5 g. of IV, m. 70-1°. (A) was extracted twice with dilute HCl. The soluble part, isolated and recrystallized from EtOH (3.5 g.), was identified as III, m. 110-11°. The insoluble residue, extracted with 25% HCl (110 ml.), gave 5 g. of an insoluble residue, recrystallized from EtOH and identified as V, m. 93-4°. Fraction (5) was shaken with 100 ml. 12% HCl, and the soluble part (C) removed from the insoluble part (D). (C) contained III. (D), recrystallized from EtOH, was identified as V. The mother liquor yielded an oil which, recrystallized from benzene, then from acetone-water, yielded VI, m. 58-9°. Fraction (10), recrystallized from EtOH, yielded 3 g. VIII, m. 106.5-7.5°. The mother liquor yielded an oil which was extracted with HCl. The residue, recrystallized from EtOH, gave needles of IX, m. 44-5°. IV was obtained from fraction (2) by again distilling under 20 mm., collecting the 99-106° fraction (55 g.), extracting with 85 ml. 8% HCl, and pouring the solution into NH4OH; the resulting 13 g. oil, recrystallized from benzene, yielded 8 g. (0.4%) of IV, m. 71-2°, decomposes on distillation IV (1 g.) was heated 8 hrs. at 160° with 10 ml. NH4OH (sp. gr. 0.9) in sealed tubes, made basic, and extracted with ether. Removal of the ether left an oil which recrystallized from benzene and ligroin with difficulty. The product, 4-amino-3-bromopyridine (X), forms a picrate, m. 235-6°, which yields X, m. 69.5-70.5°, when treated with base, distilled with steam, extracted with ether, dried, and poured into petr. ether. X (0.17 g.) in 1 ml. 20% H2SO4 was reacted with 0.20 ml. Br in 1.5 ml. HOAc, made basic, extracted with ether, the ether removed, and the residue recrystallized from aqueous EtOH, yielding 4-amino-3,5-dibromopyridine (XI). IV upon standing 8 months decomposes to form a N-pyridylpyridinium compound (XII), m. 205-9°. XII heated with NH4OH (sp. gr. 0.9) 8 hrs. in a sealed tube (200°) yielded X. IV (1 g.) heated 15 min. at 140° yielded yellow crystals which, when extracted by refluxing with EtOH, yielded 1-(3-bromo-4-pyridyl)-3-bromo-4-pyridone, m. 243-4°. 2,3,6-Tribromopyridine (1.8 g.) was reduced (2 hrs., H, Pd on Norit, 5%) in 50 ml. MeOH and 2 ml. 12% NaOH, the solution made basic and extracted with ether, the ether removed, the residue treated with 10% HCl, the solution made basic with NH4OH, and the precipitate recrystallized from aqueous EtOH, yielding VI, m. 57-8°. VI (0.35 g.) was heated at 170° in a sealed tube with 8 ml. NH4OH (sp. gr. 0.9), then made basic with NaOH and extracted with ether, the ether removed, and the residue recrystallized from ligroin, yielding 2-amino-3-bromopyridine (XIV), m. 64.5-5.5°, 0.27 g. of which, dissolved in 20% H2SO4 and mixed with 0.4 g. Br in 4.5 ml. HOAc and heated 20 min., then treated with Na2CO3 solution, yielded 0.4 g. 2-amino-3,5-dibromopyridine, m. 103-4° (from ligroin). Heating 2,4-dibromopyridine with NH4OH yielded 2-amino-4-bromopyridine (XV), m. 143-4.5° (picrate, m. 262-3°) and 4-amino-2-bromopyridine (XVI), m. 97.5-8.5° (picrate, m. 129-30°). Bromination of XVI yielded 4-amino-2,3,5-tribromopyridine, m. 147-8°, and 4-amino-2,3-dibromopyridine, m. 171-3°. 2,4-Dihydroxypyridine in 48% HBr and Br yielded 3-bromo-2,4-dihydroxypyridine (XVII), m. 263.5-4.5° (decomposition). XVII with POBr3 in a sealed tube yielded 2,3,4-tribromopyridine (XVIII), m. 84-5°. The structure was proved by synthesis of XVIII from 3-bromo-2,4-dihydroxy-5-pyridinecarboxylic acid (XIX). XIX heated with 38% HCl was converted to 3-chloro-2,4-dihydroxypyridine (decomposes 310°) which, heated with POBr3, yielded 3-chloro-2,4-dibromopyridine (XX), m. 70-70.5°. XX heated with NH4OH yielded 2-aminobromochloropyridines of unknown structure. XVIII heated with NH4OH yielded 2-amino-3,4-dibromopyridine (XXI), recrystallized from aqueous EtOH, m. 128-9°, and 4-amino-2,3-dibromopyridine (XXII), recrystallized from ligroin-EtOH, m. 173-5°. XXII reduced in basic solution (H, Pd) yielded 4-amino-pyridine, m. 158°. XVIII was also prepared from 2,4-dimethoxypyridine by heating with PBr5 and POBr3. Bromination of 2,4-dihydroxypyridine yielded 3,5-dibromo-2,4-dihydroxypyridine, which, treated with 48% HBr, yielded 2,4,5-tribromopyridine (XXIII), recrystallized from aqueous EtOH, m. 66.5-7.5°. XXIII heated with NH4OH yielded 4-amino-2,5-dibromopyridine, recrystallized from aqueous EtOH, m. 147-8°. VIII when brominated at 500° yielded 2,3,4,5-tetrabromopyridine (XXIV), recrystallized from aqueous EtOH, m. 74.5-5.5°. XXIV was also prepared by heating 2,4-dihydroxypyridine with PBr5 and POBr3 for 5.5 hrs. at 120-5°. XXIV heated with NH4OH as before yielded 4-amino-2,3,5-tribromopyridine, m. 148-8.5°. A table of constants of known bromopyridines is given. The experimental process involved the reaction of 2,4-Dibromo-3-chloropyridine(cas: 861024-77-3).Product Details of 861024-77-3

2,4-Dibromo-3-chloropyridine(cas:861024-77-3) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Product Details of 861024-77-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Sravanthi, A. L. et al. published their research in Plant Physiology Reports in 2022 |CAS: 132-20-7

N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate(cas:132-20-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Name: N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate

On March 31, 2022, Sravanthi, A. L.; Ratnakumar, P.; Reddy, S. Narender; Eswari, K. B.; Pandey, Brij B.; Manikanta, ChLN; Ramya, K. T.; Sonia, E.; Mohapatra, Shruti; Gopika, K.; Anusha, P. L.; Yadav, Praduman published an article.Name: N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate The title of the article was Morpho-physiological, quality traits and their association with seed yield in sesame (Sesamum indicum L.) indigenous collection under deficit moisture stress. And the article contained the following:

Abstract: A field experiment was conducted to investigate the effect of deficit moisture stress on eleven sesame genotypes viz., IC-132171, IC-132186, IC-204445, IC-131500, IC-132207, IC-205471, IC-203962, IC-205353, IC-96229, and IC-204966 along with a national check (GT-10). The deficit moisture stress (WS) was imposed for a period of 50-55 days from flowering to physiol. maturity. The morphol., physiol., and yield traits under WS significantly decreased in comparison with irrigated conditions (WW). Based on the mean trait performance studied among the genotypes, IC-204966 was found significantly superior with respect to plant height, capsules number, seed weight, total dry matter, leaf area, relative water content and reduced canopy temperature under WS conditions. The correlation anal. of different traits with seed yield indicated that the plant height and number of capsules/plant were highly and pos. correlated with seed yield under both WW and WS conditions. The principal component anal. (PCA) revealed that among the traits studied, number of capsules/ plant, total dry matter, stomatal conductance, transpiration rate and fatty acid i.e., palmitic acid were the most important traits that accounted for more than half of the total variation among the sesame genotypes studied. Furthermore, the scatter plot revealed that two genotypes, IC 132,207 and IC 205,471 were stable performers under both stress and irrigated conditions, whereas the performance of check GT-10 varied depending upon conditions. The experimental process involved the reaction of N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate(cas: 132-20-7).Name: N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate

N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate(cas:132-20-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Name: N,N-Dimethyl-3-phenyl-3-(pyridin-2-yl)propan-1-amine maleate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Urban, R. et al. published their research in Helvetica Chimica Acta in 1964 |CAS: 90764-84-4

4,6-Dimethoxypicolinic acid(cas:90764-84-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Electric Literature of 90764-84-4

Urban, R.; Schnider, O. published an article in 1964, the title of the article was Aminomethoxypyridines and corresponding sulfanilamides.Electric Literature of 90764-84-4 And the article contains the following content:

A number of 2-, 3-, and 4-sulfanilamidopyridines containing substituents in the pyridine ring, particularly all still unknown monomethoxy derivatives, were prepared for pharmacol. evaluation. To 10 g. Na in 185 mL. absolute MeOH was added 20 g. 2-amino-4-chloropyridine and a little Cu powder, the whole heated 12 h. at 150° in a sealed tube, cooled, diluted with H2O, filtered, and evaporated, the residue dissolved in H2O, and the product extracted with Et2O to give 10.6 g. 2-amino-4-methoxypyridine, m. 115-16° (C6H6). 2-Chloro-4-nitropyridine (16 g.), 32 g. Fe powder, and 500 mL. AcOH heated gradually with stirring until the reaction became brisk, when the reaction subsided the mixture heated 1 h. at 100°, cooled, and worked up gave 10.4 g. 4-amino-2-chloropyridine (I), m. 87-9° (C6H6-petr. ether). To 5.0 g. Na in 90 mL. absolute MeOH was added 10 g. I and a little Cu powder and the mixture heated 10 h. at 150° in a sealed tube, and worked up to give 5.4 g. 4-amino-2-methoxypyridine, m. 88-9° (C6H6-petr. ether, sublimation at 60°/0.1 mm.); Ac derivative m. 96-7° (C6H6). 5-Hydroxy-2-phenylazopyridine (II) in 400 mL. tert-BuOH added dropwise during 4 h. to 11 g. CH2N2 in 1.7 l. Et2O at – 15 to -10° with stirring, the solution allowed to reach room temperature and evaporated, the residue dissolved in C6H6, the solution worked up, and the partially crystalline product chromatographed on Al2O3 (activity II) with C6H6 gave 14.8 g. 5-MeO analog (III) of II, m. 72-3° (petr. ether). III (10 g.) in 220 mL. MeOH and 55 mL. 3N HCl hydrogenated over 10 g. 10% Pd-C (the calculated amount H was absorbed in 8 h.) and the solution filtered, concentrated, and worked up gave 4.1 g. 2-amino-5-methoxypyridine, b10 128-30°, m. 36-8°; Ac derivative (IV) m. 102-3° (C6H6-petr. ether); HCl salt m. 145-6° (MeOH-Et2O). Ac2O (2.9 mL.) added dropwise to 2.5 g. 2-amino-3-methoxypyridine (V) in 5.0 mL. anhydrous C5H5N at below 0° with stirring and worked up gave 2.9 g. Ac derivative of V, m. 102-3° (C6H6-petr. ether, C6H6 or EtOAc), mixed m.p. (with IV) 70°. 5-Bromonicotinic acid NH4 salt (270 g.) in 2 1. 25% aqueous NH3 heated 10 h. at 180° with 100 g. CuO in an autoclave, the filtered solution concentrated and treated with aqueous Cu(OAc)2, the precipitated Cu salt filtered and dissolved in dilute HCl, the solution treated with H2S, filtered, and evaporated, the residue dissolved in dilute aqueous NaOH, and the solution neutralized with dilute HCl gave 104 g. 5-aminonicotinic acid (VI), m. 295-6° (decomposition) (H2O). VI (20 g.) suspended in 400 mL. absolute MeOH saturated with HCl with ice-cooling, and the resulting solution refluxed 0.5 h. while continuously introducing HCl and cooled gave (in 2 crops) 23.8 g. Me 5-hydroxynicotinate-HCl (VII.-HCl), m. 194-6° (decomposition); 73% VII m. 192-3° (H2O). VII (8.0 g.) in 200 mL. tert-BuOH added dropwise during 6 h. to 3.5 g. CH2N2 in 350 mL. Et2O at – 15 to – 10° with stirring, the solution stirred several hrs. with cooling, allowed to reach room temperature, filtered, and concentrated, the residue dissolved in alc.-HCl, and the solution evaporated gave, after crystallization from MeOH-Et2O, 9.5 g. Me 5-methoxynicotinate-HCl (VIII.HCl), which in aqueous solution passed through a column of Amberlite IR-45 and the effluent evaporated gave 5.0 g. VIII, m. 61-2° (sublimation at 40°/0.1 mm.), saponification giving 5-methoxynicotinic acid (IX), m. 228-9°. VIII (8.0 g.), 18 mL. 100% N2H4.H2O, and 25 mL. MeOH refluxed 6 h. and cooled gave 6.8 g. hydrazide (X) of IX, m. 157-8° (MeOH). X (19.4 g.) in 125 mL. N HCl treated dropwise with 12 g. KNO2 in 40 mL. H2O at 5° with stirring and ice-cooling, the precipitated azide filtered off, washed with a little H2O, dried over P2O5, and refluxed 1 h. in 200 mL. absolute EtOH, and the solution evaporated gave 20.8 g. 5-methoxy-3-pyridinecarbamic acid Me ester, m. 139-41°, which refluxed with 40 g. Ba(OH)2 in 400 mL. H2O, the solution cooled, saturated with CO2, filtered, and worked up gave 8.0 g. 3-amino-5-methoxypyridine, b15 166-8°, m. 64-5° (C6H6); Ac derivative m. 133-4° (C6H6, EtOAc); HCl salt m. 205-7° (decomposition). Nicotinic acid-HCl (280 g.) and 500 mL. SOCl2 refluxed 6 days and then heated 12 h. at 180° in an autoclave, the mixture added to H2O, heated to boiling, and filtered hot, the filtrate cooled, and the precipitate recrystallized from H2O with C gave 130 g. mixture of 5-chloro- (XI) and 5,6-dichloronicotinic acid, which refluxed 4 h. with 52 g. red P and 130 g. KI in 800 mL. 57% HI, the solution cooled, diluted with H2O, filtered, concentrated to small volume, and treated with an appropriate amount aqueous Na2CO3 gave 78 g. XI, m. 167-8° (H2O); Me ester m. 87-8°; hydrazide (XII) m. 176-8°. XII (20 g.) dissolved in 120 mL. N HCl by heating, the solution cooled in ice, treated dropwise with 12 g. KNO2 in 40 mL. H2O at 5° with stirring, the precipitated azide filtered off, washed with H2O, heated 0.5 h. on a water bath in 220 mL. 50% AcOH, cooled, made alk. with aqueous NaOH, and cooled, and the product isolated with Et2O gave 6.0 g. 3-amino-5-chloropyridine, m. 78-9° (sublimation at 60°/0.1 mm., C6H6-petr. ether). The above azide dried over P2O5 and refluxed 1 h. with 10 volumes absolute EtOH gave 5-chloro-3-pyridinecarbamic acid Et ester, m. 149-51° (MeOH, sublimation at 70°/0.1 mm.). Na (5 g.) in 60 mL. MeOH and 16.2 g. 4,6-dichloro-2-picoline heated 12 h. at 130-40° in a sealed tube, cooled, and diluted with Et2O, and the solution filtered and fractionated gave 11.8 g. 4,6-dimethoxy-2-picoline (XIII), b17 87-8°, n23D 1.5076, m. 19-20°. XIII (11.7 g.) in 350 mL. H2O heated on a water bath, 13 g. finely powd. KMnO4 added with stirring, when the violet color disappeared 12.5 g. KMnO4 and 70 mh H2O added, the mixture heated 2.5 h., cooled a little, the MnO2 filtered off and washed with hot H2O, the combined cooled filtrates extracted with Et2O (6 g. XIII recovered), acidified with HCl, and evaporated, the residue (XIV) extracted (Soxhlet) exhaustively with C6H6, and the extract evaporated gave 1.2 g. 4,6-dimethoxypicolinic acid (XV), m. 145-7° (C6H6, sublimation at 90°/0.1 mm.). It was preferable not to isolate XV, but to convert XIV directly into the Me ester (XVI) of XV (20% yield). XV (1.2 g.) in 40 mL. absolute MeOH saturated with HCl with ice-cooling, the solution evaporated, the residue extracted with Et2O, and the extract worked up gave 1.1 g. XVI, m. 108-9° (C6H6, sublimation at 60°/0.1 mm.). Na (3.3 g.) in 50 mL. absolute MeOH refluxed 8 h. with 10.0 g. Me 4,6-dichloropicolinate and a little Cu powder, the filtered solution evaporated, and the residue extracted with Et2O gave 4.8 g. XVI, m. 106-8°. XVI (18 g.) in 100 mL. MeOH treated with 33 mL. 100% N2H4.H2O gave 17 g. hydrazide (XVII) of XV, m. 156-7° (MeOH). H2O (35 mL.) containing 8.0 g. KNO2 added dropwise during 1.5 h. to 15 g. XVII suspended in 80 mL. N HCl with stirring and ice-cooling, the precipitated azide filtered off, washed with a little H2O, dried over P2O5, and refluxed 1 h. in 160 mL. absolute EtOH, the solution filtered [1.9 g. insoluble fraction (A) recovered] and evaporated, the residual urethane compound (13 g.) refluxed 6 h. with 37 g. Ba(OH)2.8H2O in 150 mL. H2O, the cooled solution saturated with CO2, filtered, and evaporated, and the residue worked up gave 6.3 g. 2-amino-4,6-dimethoxypyridine, b12 145-7°, m. 69-70°; fraction A crystallized from HCONMe2-H2O or a large volume C6H6 gave bis(4,6-dimethoxypicolinoyl)hydrazine, m. 228-30°. From 15 g. hydrazide of 2,6-dimethoxyisonicotinic acid was prepared similarly 5.5 g. 4-amino-2,6-dimethoxypyridine, m. 82-3° (C6H6-petr. ether); the intermediate 2,6-dimethoxy-4-pyridinecarbamic acid Et ester m. 58-60°. Na (17.5 g.) in 350 mL. absolute MeOH and 35 g. 3-amino-2,6-dibromopyridine heated 15 h. at 130-5° in a sealed tube, the solution evaporated, and the residue dissolved in a little H2O and worked up gave 6.3 g. 3-amino-6-bromo-2-methoxypyridine (XVIIa), m. 78-9° (sublimation at 50°/0.1 mm., dilute MeOH) [86% Ac derivative (XVIII) m. 147-8° (EtOAc)], and 4.65 g. 3-amino-2,6-dimethoxypyridine, b10 116-17°, m. 43-5° [Ac derivative m. 85-7° (EtOAc, sublimation)]. XVIII (2.45 g.) in 65 mL. MeOH was hydrogenated over Pd-C in the presence of 4.0 g. NaOAc.3H2O (the calculated amount H was absorbed rapidly), the filtered solution evaporated, the residue extracted with Et2O, and the extract worked up to give 1.6 g. 3-acetamido-2-methoxypyridine, m. 88-9° (sublimation, C6H6-petr. ether). 2,4-Dichloro-6-methyl-3-nitropyridine (XIX) (20 g.) in 100 mL. MeOH added dropwise to 7.0 g. Na in 100 mL. absolute MeOH with stirring, the solution refluxed 8 h. and evaporated, the residue partitioned between H2O and C6H6, and the organic layer worked up gave 16 g. 2,4-dimethoxy-6-methyl-3-nitropyridine (XX), m. 105-7° (C6H6-petr. ether). XX (10 g.) in 100 mL. MeOH hydrogenated over 5 g. 5% Pd-C (the calculated amount H was absorbed in 3 h.) and the filtered solution fractionated gave 7.3 g. 3-amino analog of XX, b15 140-1°; HCl salt m. 163-4° (MeOH-Et2O). XIX (10 g.) in 70 mL. absolute MeOH added dropwise to 1.2 g. Na in 25 mL. absolute MeOH with stirring, the solution stirred several hrs. at room temperature, kept overnight, filtered, and evaporated, and the residue recrystallized from 3.5 l. H2O gave 7.6 g. 2(or 4)-chloro-4(or 2)-methoxy-6-methyl-3-nitropyridine (XXI), m. 103° (MeOH). XXI (10 g.) in 200 mL. MeOH hydrogenated over 3 g. 5% Pd-C (the calculated amount H was absorbed in 3-4 h.), the filtered solution evaporated, and the residue made alk. with aqueous NaOH and extracted continuously with C6H6 gave 3.8 g. 3-amino-2(or 4)-methoxy-6-methylpyridine, m. 74-5° (C6H6-petr. ether). 2,4-Dichloro-6-methylpyridine (65 g.), 200 mL. absolute EtOH, and 200 g. liquid NH3 heated 24 h. at 150° in an autoclave, the solution cooled, filtered, and evaporated, the residue dissolved in H2O, the solution saturated with K2CO3 and extracted with hot C6H6, and the extract kept deposited 18 g. 4-amino-2-chloro-6-methylpyridine (XXII), m. 155-7° (C6H6, H2O); from the aqueous mother liquors of XXII was isolated 4.8 g. 2,4-diamino-6-methylpyridine, m. 117-18°; all the C6H6 mother liquors combined and evaporated, and the residue recrystallized from 50 volumes H2O gave 11.5 g. 2-amino-4-chloro-6-methylpyridine (XXIII), m. 108-9° (C6H6). XXIII (2.85 g.) in 130 mL. MeOH hydrogenated over Pd-C in the presence of NaOAc.3H2O (the calculated amount H was absorbed rapidly), the filtered solution evaporated, the residue dissolved in H2O, the solution made alk. with concentrated aqueous NaOH, and the product isolated with Et2O gave 1.45 g. 2-amino-6-methylpyridine, b15 105-6°, m. 41-2°; HCl salt m. 155-6°. From XXII was similarly prepared 4-amino-2-methylpyridine, m. 93-5° (C6H6-petr. ether). Na (4.8 g.) in 90 mL. MeOH heated 12 h. at 130-40° with 8.0 g. XXIII and a little Cu powder in a sealed tube, the solution cooled, filtered, and evaporated, and the residue sublimed at 100°/0.1 mm. gave 5.65 g. 4-MeO analog of XXIII, m. 141-2° (C6H6). XXII treated similarly, the crude product sublimed, and the impure sublimate chromatographed on Al2O3 (activity III) with C6H6 gave 5.1 g. 2-MeO analog of XXII, m. 98-9°. 4-AcNHC6H4SO2Cl (XXIIIa) (14.8 g.) added to 15.1 g. 4-amino-3-methoxypyridine (XXIV) in 50 mL. dioxane with stirring, the mixture heated 0.5 h. at 90-5°, added to H2O-MeOH, the solution concentrated to a small volume and diluted with H2O, the precipitate filtered off (from the mother liquor was isolated 9.75 g. unchanged XXIV) and dissolved in dilute aqueous NaOH, and the solution decolorized with bone black and treated with CO2 gave 11.3 g. 4-(4-acetylsulfanilamido)-3-methoxypyridine, m. 232-3° (MeOH). 4-O2NC6H4SO2Cl (7.2 g.) added portionwise to 6.0 g. XVIIa in 50 mL. anhydrous C5H5N with stirring, the solution heated 2.5 h. at 70°, cooled, and evaporated, the residue dissolved in H2O, the solution acidified with AcOH, the precipitate dissolved in dilute aqueous NaOH, and the solution treated with bond black, and saturated with CO2 gave 9.8 g. 6 – bromo – 2 – methoxy – 3 – (4 – nitrobenzenesulfonamido)pyridine (XXV), m. 165-7°. XXV (9.8 g.), 31 g. Fe powder, 1 mL. 20% HCl, and 100 mL. MeOH refluxed and stirred 9 h., the solution filtered hot, the filter cake washed with MeOH, the combined filtrates evaporated, the residue dissolved in dilute aqueous NaOH, the solution filtered and saturated with CO2, and the precipitate worked up gave 5.5 g. 3-sulfanilamido analog of XXV, m. 172-3° (dilute MeOH). The appropriate aminopyridine (0.1 mol) in 100 mL. anhydrous C5H5N treated portionwise with 0.12 mol XXIIIa with stirring, the solution heated 2 h. at 70° or stirred 6 h. at room temperature and evaporated in vacuo, the residue treated with H2O, the precipitate filtered off, washed with H2O, and dissolved in dilute aqueous NaOH, and the solution treated with bone black and saturated with CO2 gave 63-90% N4-acetylsulfanilamidopyridines (XXVI), which were recrystallized from MeOH or dilute MeOH or HCONMe2-H2O. The appropriate XXVI (0.1 mol) in 120 mL. 2N NaOH refluxed 1 h., the solution cooled and acidified with AcOH, and the crude product purified gave 76-94% sulfanilamidopyrimidines, which were recrystallized from MeOH or dilute MeOH. The following 2-sulfanilamido compounds (XXVII) were prepared (Z, R, R1, R2, R3, % yield, m.p. given): Ac, OMe, H, H, H, 69, 212°; Ac, H, OMe, H, H, 63, 262-3°; Ac, H, H, OMe, H, 90, 228-30°; Ac, H, OMe, H, OMe, 90, 201-3°; Ac, H, OMe, H, Me, 58, 236-8°; H, OMe, H, H, H, 85, 214-15°; H, H, OMe, H, H, 76, 237-9°; H, H, H, OMe, H, 93, 200-1°; H, H, OMe, H, OMe, 92, 158-9°; H, H, OMe, H, Me, 72, 184-5°. Also prepared were the following 3-sulfanilamidopyridines (XXVIII) (same data given): Ac, OMe, H, H, H, 63, 194-5°; Ac, H, OMe, H, H, 73, 257-8°; Ac, H, H, OMe, H, 75, 253-4°; Ac, H, H, Br, H, 88, 250-1°; Ac, H, H, Cl, H, 72, 255-6°; Ac, OMe, H, H, OMe, 85, 193-5°; Ac, OMe, H, H, Br, 78, 210-11°; Ac, OMe, OMe, H, Me, 68, 236-7°; Ac, H (or OMe), OMe (or H), H, Me, 61, 228-9°; H, OMe, H, H, H, 82, 134-6°; H, H, OMe, H, H, 90, 222-3° (dilute HCONMe2); H, H, H, OMe, H, 85, 220-1°; H, H, H, Br, H, 92, 208-10°; H, H, H, Cl, H, 87, 208-9°; H, OMe, H, H, OMe, 94, 165-7°; H, OMe, H, H, Br, 61, 172-3°; H, OMe, OMe, H, Me, 90, 225-7°; H, H (or OMe), OMe (or H), H, Me, 90, 210-11°. Also prepared were the following 4-sulfanilamidopyridines (XXIX) (same data given): Ac, OMe, H, H, H, 72, 218-19°; Ac, H, OMe, H, H, 77, 232-3°; Ac, OMe, H, OMe, H, 84, 230-1°; Ac, OMe, H, Me, H, 81, 204-5°; H, OMe, H, H, H, 86, 151-2°; H, H, OMe, H, H, 89, 173-4° (hydrate); H, OMe, H, OMe, H, 84, 181-2°; H, OMe, H, Me, H, 71, 69-71° (methanolate). The monomethoxy-substituted 2- and 4-sulfanilamidopyridines and the 5-substituted 3-sulfanilamidopyridines had a strong chemotherapeutic action against various bacteria in the mouse and rat, but this action did not approach that of 6-sulfanilamido-2,4-dimethoxypyrimidine. The 3-sulfanilamidopyridines having an MeO group in the 2- or 4-position and all the disubstituted sulfanilamidopyridines were inactive or had little activity. The experimental process involved the reaction of 4,6-Dimethoxypicolinic acid(cas: 90764-84-4).Electric Literature of 90764-84-4

4,6-Dimethoxypicolinic acid(cas:90764-84-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Electric Literature of 90764-84-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Popp, Frank D. et al. published their research in Journal of the American Chemical Society in 1958 |CAS: 98488-99-4

4-Bromo-5-ethyl-2-methylpyridine(cas:98488-99-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Reference of 4-Bromo-5-ethyl-2-methylpyridine

Popp, Frank D.; McEwen, Wm. E. published an article in 1958, the title of the article was Approaches to the synthesis of emetine from Reissert compounds.Reference of 4-Bromo-5-ethyl-2-methylpyridine And the article contains the following content:

2-Methyl-4-nitro-5-ethylpyridine 1-oxide (94 g.) and 325 cc. PBr3 yielded by the method of Lee and Swan (C.A. 50, 13918g) 53% 2-methyl-4-bromo-5-ethylpyridine (I), b0.9 55-7°. EtBr added slowly with stirring to 36.48 g. Mg and 75 cc. dry Et2O, the mixture treated after the initial reaction had subsided with 108.5 g. I and 99.4 g. EtBr in 300 cc. dry Et2O at such a rate as to maintain gentle reflux, refluxed 2 hrs., the Et2O distilled, the residue diluted with 375 cc. dry C6H6, cooled, treated with 222.3 g. HC(OEt)3, refluxed 2 hrs., kept 15 hrs. at room temperature, treated with 500 cc. aqueous NH4Cl, the aqueous layer extracted with Et2O, the Et2O layer extracted with 1 l. N H2SO4 in portions, the acidic extract basified with aqueous NaHCO3, extracted with Et2O, and the extract worked up yielded 44.36 g. di-Et acetal (II) of 2-methyl-5-ethyl-4-pyridinecarboxaldehyde (III), b3 109-14°; picrate, m. 139-40° (EtOH) (all m.ps. are corrected). II (11.15 g.) in 90 cc. 10% HCl refluxed 2 hrs. under N, kept 16 hrs. at room temperature, basified with aqueous Na2CO3, extracted with CHCl3, and the extract worked up gave 6.57 g. III, b1 64-8°; oxime, m. 143-4° (EtOH). 3-Ethyl-4-methylpyridine was converted by the method of Berson and Cohen (C.A. 50, 9405i) to 69% 1-oxide (IV), b3 142-9°; picrate, m. 141.5-2.5° (EtOH). IV (186 g.) added slowly to 380 cc. warm Ac2O, refluxed 4 hrs., and evaporated gave 154 g. (3-ethyl-4-pyridyl)methanol acetate (V), b2.5 108-15°; picrate, m. 137-8° (EtOH). V (44.7 g.), 25 cc. 30% H2O2, and 115 g. glacial AcOH heated 4 hrs. on the steam bath, treated again with 21 cc. H2O2, heated 4 hrs., kept 36 hrs. at room temperature, evaporated in vacuo, the residue treated with 125 cc. Ac2O, heated 5.5 hrs. on the steam bath, concentrated in vacuo, treated with 175 cc. 6N HCl, refluxed 2 hrs., concentrated in vacuo, neutralized with aqueous NaOH, extracted with Et2O, and the extract worked up gave 10.2 g. 3-ethyl-4-pyridinecarboxaldehyde (VI), b2.5 71-5°; oxime, m. 146.5-8.5° (EtOH). VI (11.25 g.) and 52 cc. 13.5% alc. HBr kept 88 hrs. at room temperature, diluted with a large volume of C6H6, dried azeotropically during 24 hrs., evaporated, the residue basified with aqueous K2CO3, and the product isolated with Et2O gave 9.47 g. di-Et acetal (VIII) of VI, b1.9 100-2°; picrate, m. 115-16° (EtOH). 2-(p-Anisoyl)-6,7-dimethoxy-1,2-dihydroisoquinaldonitrile (VIII) (8.75 g.) in 45 cc. dry dioxane and 15 cc. dry Et2O treated at -20° under N slowly with stirring with PhLi (from 4.40 g. PhBr) in Et2O, then slowly with 3.38 g. VI, stirred 20 min. at -20° and 7 hrs. at room temperature, washed with H2O, 0.5N HCl, and H2O, distilled, and the gummy residue crystallized from EtOH gave 0.20 g. 6,7-dimethoxyisoquinaldonitrile (IX), m. 198.4-9.0° (EtOH); the HCl extract basified with aqueous NaOH, extracted with Et2O, the extract evaporated, and the gummy residue treated with EtOH gave 3.31 g. 1-(6,7-dimethoxyisoquinolyl)-4-(3-ethyl-4-pyridyl)carbinyl β-anisate (X), m. 248.2-8.7° (EtOH); the EtOH filtrate refluxed 2 hrs. with 2.8 g. KOH in 20 cc. H2O, the EtOH evaporated in vacuo, the aqueous residue extracted with Et2O, the precipitate filtered off, the extract evaporated, and the combined solids recrystallized from EtOH gave 1.57 g. 1-(6,7-dimethoxyisoquinolyl)-4-(3-ethyl-4-pyridyl)carbinol (XI), m. 168-9° (EtOH); the aqueous filtrate acidified gave 0.93 g. p-MeOC6H4CO2H. IX (0.02 g.) and 4.0 g. polyphosphoric acid heated 1 hr. on the steam bath, diluted with 10 cc. iced H2O, and neutralized with aqueous KOH gave 0.02 g. 6,7-dimethoxyisoquinaldamide, m. 169-70° (EtOH). 2-Benzoyl-6,7-dimethoxy-1,2-dihydroisoquinaldonitrile (1.45 g.) and 6 cc. SOCl2 heated 3 hrs. on the steam bath, evaporated in vacuo, the residue diluted with 35 cc. H2O, basified with aqueous NaOH, and the precipitate filtered off yielded 0.8 g. IX, m. 198.4-9.0° (EtOH). X (2.96 g.), 0.95 g. KOH, 25 cc. EtOH, and 55 cc. H2O refluxed 5 hrs., the EtOH evaporated in vacuo, and the aqueous residue filtered off gave 2.01 g. XI; the aqueous filtrate acidified gave 98% p-MeOC5H4CO2H. XI (0.5 g.), 0.5 g. Na2Cr2O7, and 10 cc. 80% AcOH stirred 1 hr. at room temperature, basified with aqueous NaHCO3, and extracted with CHCl3 gave 0.44 g. 1-(6,7-dimethoxyisoquinolyl) 3-ethyl-4-pyridyl ketone, m. 152-3° (ligroine). VIII (13.31 g.) in 70 cc. dry dioxane and 60 cc. dry Et2O treated under N at -25° slowly with stirring with PhLi from 6.60 g. PhBr in Et2O, then slowly with 5.70 g. III, stirred 1 hr. at -20°, kept 15 hrs. at room temperature, extracted with N HCl, washed, and the organic layer evaporated gave 4.06 g. IX; the HCl extract basified with aqueous NaOH, extracted with Et2O, the extract evaporated, the gummy residue (13.1 g.) dissolved in EtOH, the solution treated with 4.5 g. KOH in 30 cc. H2O, refluxed 1.5 hrs., the EtOH distilled, the aqueous distillation residue extracted with Et2O, and the extract worked up gave 3.95 g. 1-(6,7-dimethoxyisoquinolyl)(2-methyl-5-ethyl-4-pyridyl)carbinol, m. 174-5° (EtOH). 4-Pyridinecarboxaldehyde (XII) (50.0 g.) and 185 cc. 11.5% alc. HCl kept 90 hrs. at room temperature, diluted with 450 cc. dry C6H6, distilled with the azeotropic removal of the EtOH and H2O, the distillation residue basified with aqueous K2CO3, extracted with Et2O, and the extract worked up yielded 37.0 g. di-Et acetal (XIV) of XII, b6 99-100°. XIV (9.06 g.) and 9.25 g. Ph(CH2)2Br in 35 cc. dry xylene heated 1 hr. on the steam bath, the xylene solution decanted from a gummy precipitate, allowed to stand several days, diluted with a small amount of EtOH and a large amount of Et2O to precipitate more gum, and the combined precipitates crystallized from Et2O-EtOH gave 12.8 g. 1-phenethyl-4-(diethoxymethyl)pyridinium bromide (XV) dihydrate, m. 65.6-6.5°, which turned to a gum when dried over H2SO4 in vacuo; XV picrate, m. 104.6-5.6°. XV.2H2O (2.50 g.) in 25 cc. H2O treated with 8.8 g. K3Fe(CN)6 in 25 cc. H2O, kept overnight, diluted with 25 cc. C6H6, treated slowly with stirring at room temperature with 4.0 g. NaOH in 40 cc. H2O, stirred 1 hr., the aqueous layer extracted with C6H6, and the extract worked up gave 0.95 g. 1-phenethyl-4-(diethoxymethyl)-2(4H)-pyridone (XVI), m. 84.0-4.5°. 3,4-(MeO)2C6H3(CH2)2OH and PBr3 yielded 63% 3,4-(MeO)2C6H3(CH2)2Br (XVIII), b1.5 122-9°, m. 42-8°. XIV (3.62 g.) and 4.90 g. XVII heated 20 min. on the steam bath, kept overnight, and the gummy product treated with a small amount of EtOH and a large amount of Et2O yielded 4.90 g. 3,4-(MeO)2C6H3(CH2)2 analog (XVIII) of XV, m. 79-81.5°; picrate, m. 115.2-16.0° (EtOH). XVIII (2.83 g.) gave similarly 1.35 g. gummy product which, treated in EtOH, with a few drops of H2SO4, then with 2,4-(O2N)2C6H3NHNH2 solution, gave the 2,4-dinitrophenylhydrazone of 1-(3,4-dimethoxyphenethyl)-4-formyl-2(1H)-pyridone (XVIIIa), m. 270.0-70.8° (hot EtOH and hot Me2CO). VII (5.50 g.) and 6.44 g. XVII gave in the usual manner 90% 1-(3,4-dimethoxyphenethyl)-3-ethyl-4-(diethoxymethyl)pyridinium bromide (XIX), m. 140-1°; picrate, m. 126.3-7.1° (EtOH). XIX (4.54 g.) treated in the usual manner with K3Fe(CN)6 and the crude gummy product (2.90 g.) treated with EtOH, a few drops of H2SO4, and 2,4-(O2N)2C6H3NHNH2 solution yielded the 2,4-dinitrophenylhydrazone of the 3-Et derivative of XVIIIa, orange crystals, m. 268-9° (hot EtOH and hot Me2CO). 2-Methyl-5-ethyl-4-pyridinecarboxaldehyde di-Et acetal (3.41 g.) and 3.75 g. XVII yielded in the usual manner 43% 1-(3,4-dimethoxyphenethyl)-2-methyl-4-(diethoxymethyl)-5-ethylpyridinium bromide, m. 150.5-2.0° (Et2O-EtOH). The experimental process involved the reaction of 4-Bromo-5-ethyl-2-methylpyridine(cas: 98488-99-4).Reference of 4-Bromo-5-ethyl-2-methylpyridine

4-Bromo-5-ethyl-2-methylpyridine(cas:98488-99-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Reference of 4-Bromo-5-ethyl-2-methylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Kritchevsky, D. et al. published their research in Archives Internationales de Pharmacodynamie et de Therapie in 1964 |CAS: 636-73-7

Pyridine-3-sulfonic acid(cas:636-73-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Category: pyridine-derivatives

Kritchevsky, D.; Tepper, S. A. published an article in 1964, the title of the article was Oxidation of cholesterol-26-14C by rat liver mitochondria: effect of compounds related to nicotinic acid and nicotinamide.Category: pyridine-derivatives And the article contains the following content:

cf. CA 58, 840f. Nicotinamide homologs were tested to determine their effect on the oxidation of labeled cholesterol and compared to nicotinic acid; also examined were ω-3-pyridylacrylic acid and picolinic and 3-pyridinesulfonic acids. The reaction mixtures were prepared according to Kritchevsky, et al. (CA 54, 11177d; 11204i), and Whitehouse, et al. (CA 53, 9422b). The percentage oxidation of cholesterol-26-14C was calculated as counts per min. of 14CO2 (as Ba14CO3) evolved during an 18-hr. incubation at 37° per 100 counts per min. of cholesterol-26-14C. Nicotinic acid showed high oxidation enhancing, but none of the amides (acetyl, propionyl, and acrylyl) had any effect. Data indicate that a free carboxyl group is necessary for stimulation of oxidation Picolinic and 3-pyridinesulfonic acids enhanced oxidation to a small extent while ω-3-pyridylacrylic acid had no in vitro effect. The nonacting compounds had no chelating action. The experimental process involved the reaction of Pyridine-3-sulfonic acid(cas: 636-73-7).Category: pyridine-derivatives

Pyridine-3-sulfonic acid(cas:636-73-7) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Robison, Michael M. et al. published their research in Journal of the American Chemical Society in 1955 |CAS: 156267-13-9

N,3-Dimethylpyridin-2-amine(cas:156267-13-9) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 156267-13-9

Robison, Michael M.; Robinson, Bonnie L. published an article in 1955, the title of the article was 7-Azaindole. II. Conversion to 7-methyl-7H-pyrrolo-[2,3-b]pyridine and related compounds.Related Products of 156267-13-9 And the article contains the following content:

cf. C.A. 50, 1019g. 7-Azaindole (I) (5.90 g.) [prepared by a slight modification of the method described previously (loc. cit.)] in 75 cc. dry C6H6 refluxed 50 min. with 11.1 g. p-MeC6H4SO3Me, cooled, kept overnight, and filtered, the solid washed with EtOAc, and the white crystalline product (14.07 g.) dissolved in boiling CHCl3, diluted to turbidity with EtOAc, and cooled yielded 7-methyl-1H-pyrrolo[2,3-b]pyridinium p-toluenesulfonate (II), prisms, m. 134.0-4.5° (all m.ps. are corrected). I kept 3 days with 4 equivalents MeI, the excess MeI evaporated, and the residue washed with Et2O gave 100% impure 7-methyl-1H-pyrrolo[2,3-b]pyridinium iodide (III), m. 80-150°. Crude II (7.60 g.) in 15 cc. H2O saturated with cooling with K2CO3 and extracted with 600 cc. Et2O in 10 portions, the extract dried and evaporated, the brown oily residue in the min. amount hot 1:1 C6H6-hexane, treated with Darco, and evaporated on the steam bath, the residue chilled, and the yellow-brown solid residue dried in vacuo over KOH and distilled in a sublimation apparatus at 80-90° (bath) and 0.2 mm. yielded 2.31 g. crude 7-methyl-7H-pyrrolo[2,3-b]pyridine (IV), yellow solid, which dried in the m.p. tube in vacuo several months showed a m.p. of 48.5-50.5° (sealed tube); it liquefied rapidly in air; pKb 5.2. III gave similarly 88% 7H-pyrrolo[2,3-b]-pyridine, λ 245 (4.197), 309 (3.945), 385 mμ (log ε 2.991); pKb 5.1. The amine (0.31 g.), m. 44-6°, from the hydrolysis of II, and 20 cc. 20% aqueous NaOH refluxed 5.25 h., cooled, and extracted with Et2O, and the residue from the extract dried in vacuo over KOH yielded 0.28 g. IV, m. 44-6°. II (1.38 g.) in 15 cc. H2O treated with 1.14 g. picric acid and 0.41 g. anhydrous NaOAc yielded the picrate of IV, lemon-yellow needles, m. 209.5-10.5°. I (273 mg.) refluxed 6 h. with 20 cc. aqueous NaOH and extracted with Et2O gave 258 mg. unchanged I. IV (692.5 mg.) in 50 cc. 95% EtOH hydrogenated 25.5 h. at atm. pressure over 340 mg. Pt (reduced PtO2), the resulting yellow oil (506 mg.) in 10 cc. dry C6H6 kept 65 min. at room temperature with 429 mg. PhNCO, the C6H6 evaporated on the steam bath in a N stream, the residue warmed slightly with a few cc. H2O and 5 cc. 5% HCl, the solution filtered, the filtrate treated with Darco and basified strongly with excess K2CO3, the resulting oil chilled and scratched, and the solid washed and dried yielded 0.76 g. 1-phenyl-3-[2-(1-methyl-3-piperidyl)ethyl]urea (IVa), m. 100.5-2.0° (from cyclohexane) (sealed tube). 3-Pyridineacetonitrile (5.88 g.) in 80 cc. 95% EtOH and 20 cc. concentrated NH4OH hydrogenated 7 h. at 2 atm. pressure over 2-3 g. Raney Ni, filtered, the EtOH evaporated on the steam bath, the residual solution saturated with K2CO3 and extracted with CHCl3, and the extract distilled yielded 4.21 g. 3-(2-aminoethyl)pyridine (V), liquid, b15 114-19°. V treated with 2 equivalents picric acid in hot H2O gave the dipicrate, yellow needles, m. 213.5-14.0° (decomposition). V (1.22 g.) in 10 co. dry C6H6 treated 0.5 h. with 1.19 g. PhNCO and the product washed with C6H6 and dried in vacuo yielded 2.33 g. 1-phenyl-3-[2-(3-pyridyl)ethyl]urea (VI), needles, m. 114.5-15.5° (from 1:9 EtOH-H2O and from C6H6). VI (1.61 g.) and 9.5 g. MeI kept 26 h. under N, the excess MeI decanted, and the residue dried in vacuo yielded 3.07 g. 1-methyl-3-[2-(3-phenylureido)ethyl]pyridinium iodide (VII), hygroscopic, prisms, m. 71.5-4.5° (sealed tube) (from absolute EtOH). VII (1.485 g.) in 60 cc. 95% EtOH hydrogenated 8 h. at atm. pressure over 340 mg. prereduced PtO2, the resulting product dissolved in dilute HCl, filtered, and treated with excess K2CO3, and the oil rubbed gave 853 mg. IVa, m. 99.5-100.5° (sealed tube). Com. NaNH2 (1.95 g.) (finely powd.) in 100 cc. dry xylene treated dropwise with stirring with 5.90 g. I in 50 cc. dry xylene, the mixture refluxed 8 h., cooled to room temperature, treated with stirring during 0.5 h. with 7.1 g. MeI in 50 cc. xylene, refluxed 2 h., kept overnight at room temperature, and diluted with 75 cc. H2O and 20 cc. concentrated HCl, the xylene layer extracted with dilute acid, the combined aqueous extracts washed with Et2O, basified with solid K2CO3, and extracted with 600 cc. Et2O in 6 portions, the extract dried and evaporated, and the residue distilled, the resulting 4 g. mixture washed with cyclohexane, steam distilled, treated with K2CO3, extracted with Et2O, and distilled gave 1.28 g. 1-methyl-7-azaindole (VII), hygroscopic oil, b21 112-16°, nD26 1.5959, d22 1.107; it developed a yellow color on standing. 2-Amino-3-picoline (21.6 g.) in 100 cc. dry Et2O refluxed 2 h. with 7.8 g. NaNH2, cooled to room temperature, treated with 28.4 g. MeI in 50 cc. dry Et2O with stirring during 35 min., refluxed 1 h., cooled, diluted with 40 cc. H2O, and treated with excess K2CO3, the aqueous layer extracted with Et2O, and the extract dried and distilled gave 20.75 g. crude alkylation product, yellow oil, b22 105-15°; 65.94 g. crude product in 200 cc. dry pyridine treated with cooling and swirling during 12 min. with 170.2 g. BzCl, heated 0.5 h., cooled, poured below 10° into 250 cc. concentrated HCl and 790 cc. H2O, and filtered, the filtrate basified and extracted with Et2O, and the extract distilled gave 85.36 g. N-methyl-N-(3-methyl-2-pyridyl)benzamide (VIII), b22 210° to b20 220° needles, m. 92.0-3.5° (from 1:1 EtOH-H2O and from hexane). VIII (85.36 g.) refluxed 1 h. with 202 cc. concentrated HCl, cooled, filtered, basified strongly with K2CO3, and extracted with Et2O, and the extract dried and distilled gave 82.6% pure 2-methylamino-3-picoline (IX), hygroscopic oil, b21 113°, m. about 21°. IX (32.96 g.) formylated by the method of Clemo and Swan (C.A. 40, 581.1), the volatile materials distilled off after 2 days up to 60° (23 mm.), the residue dissolved in 65 cc. H2O, treated with excess K2CO3, and extracted with Et2O, and the extract dried and distilled gave 26.38 g. N-methyl-N-(3-methyl-2-pyridyl)formamide (X), oil, b19 151-56°. X added to PhNHNa and HCO2K, the reaction carried out in the usual manner (loc. cit.), the mixture treated with H2O and AcOH, and steam distilled, the distillate treated with excess HCl, decolorized with Darco, treated with excess Ac2O and NaOAc, and filtered, the filter residue washed with H2O and dilute HCl, and the combined filtrates basified with K2CO3 did not give any liquid product. X treated with 1.5 mol KOEt by the method of Tyson (C.A. 35, 5889.9) 0.5 h. at 350°, the dark mixture cooled, decomposed with H2O, and steam distilled, the distillate acidified with HCl, washed with Et2O, basified with K2CO3, and extracted with Et2O, the extract dried and distilled, and the distillate, b18 108-12°, nD30 1.5665, treated with BzCl, poured into aqueous K2CO3, allowed to stand 40 min., and extracted with Et2O gave the benzoate of IX, b19 212°, m. 91.5-96°. IV (0.52 g.) kept 28 h. with 5 cc. MeI under N, the excess MeI evaporated, and the solid residue dried gave 1.37 g. impure 1,7-dimethyl-1H-pyrrolo[2,3-b]pyridinium iodide (XI), white needles, m. 249.5° (decomposition), λ 227 (4.522), 296 μ (log ε 3.888). VII (652 mg.) treated 60 h. under N with 5 cc. MeI, the excess MeI evaporated in a N stream, and the residue washed with cyclohexane gave 597 mg. XI; m. 250.5° (decomposition) (from absolute EtOH); the cyclohexane washings evaporated gave 275 mg. VII. The UV absorption spectra of I, IV, VII, and 7-azaskatole are recorded. The experimental process involved the reaction of N,3-Dimethylpyridin-2-amine(cas: 156267-13-9).Related Products of 156267-13-9

N,3-Dimethylpyridin-2-amine(cas:156267-13-9) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Related Products of 156267-13-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lee, T. B. et al. published their research in Journal of the Chemical Society in 1956 |CAS: 98488-99-4

4-Bromo-5-ethyl-2-methylpyridine(cas:98488-99-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: 98488-99-4

Lee, T. B.; Swan, G. A. published an article in 1956, the title of the article was The constitution of yohimbine and related alkaloids. IX. Synthesis of 2-(4,5-diethyl-2-pyridyl)-3-ethylindole (alstyrine or coryline) and two related compounds.Recommanded Product: 98488-99-4 And the article contains the following content:

cf. C.A. 49, 12496a. Synthetic 2-(4,5-diethyl-2-pyridyl)-3-ethylindole and 4,5-diethylpyridine-2-carboxylic acid were identical with the appropriate degradation products of the Alstonia alkaloids and of corynantheine. Synthetic 3-ethyl-2-(5-ethyl-2-pyridyl)-5-methoxyindole did not appear to be identical with the degradation product from aricine. The 4-ethyl derivative of this was also synthesized. Adding 54 cc. 30% H2O2 to 86 g. 5-ethyl-2-methylpyridine in 250 cc. HOAc, after 5 hrs. at 70°, adding 40 cc. 30% H2O2 and keeping at 70-80° 15 hrs. gave a solution which on concentration in vacuo to 100 cc., addition of 100 cc. H2O and evaporation almost to dryness gave a residue which on basification (Na2CO3) and CHCl3 extraction afforded 52 g. 5-ethyl-2-methylpyridine N-oxide (I), b2 124-8°; picrate, m. 107-8°. Dropwise addition of a solution of 52 g. I in 98 cc. H2SO4 to a stirred mixture of 156 cc. H2SO4 and 175 cc. HNO3 (d. 1.2) at room temperature, followed by heating to 90-100° 3 hrs., cooling, and adding dropwise to stirred ice-NH4OH (d. 0.880) yielded 48 g. 5-ethyl-2-methyl-4-nitropyridine N-oxide, m. 80°. A solution of 10 g. of this in 50 cc. C6H6 on dropwise addition of 50 cc. PBr3 followed by refluxing 7 hrs. on a 125-40° bath gave a product which poured on ice, followed by basification (10% NaOH) and CHCl3 extraction gave 6.6 g. 4-bromo-5-ethyl-2-methylpyridine (II), b20 105-10°; picrate, m. 141-2° (decomposition); methiodide, m. 167-9°. Addition to a solution of 20 g. CuCN and 46 g. KCN in 180 cc. H2O of 28 g. II in 120 cc. EtOH followed by heating (autoclave, 180-200°, 4 hrs.), adjustment (concentrated HCl) to pH 4, removal of CuCN, evaporation to dryness, and drying by evaporation 3 times with EtOH gave a solid which on solution in 100 cc. EtOH, saturation with dry HCl, keeping overnight followed by 4 hrs. refluxing, removal of EtOH, basification and extraction afforded 12.15 g. Et 5-ethyl-2-methylpyridine-4-carboxylate (III), b2 112-15°; picrate, m. 129-30° (Berson and Cohen, C.A. 50, 9405i). Hydrolysis (20% KOH, reflux 90 min.) of III followed by adjustment to pH 4 gave by Et2O extraction the free acid, m. 226-8°, after purification by sublimation (140°/0.1 mm.). Addition of 12.5 g. III and 32 cc. EtOAc to KOEt (from 6.3 g. K) in C6H6 followed by 12 hrs. refluxing and addition of 140 cc. H2O gave a solution which after Et2O washing (to remove uncondensed ester), addition of 280 cc. concentrated HCl, heating overnight on a water-bath, evaporation to dryness, basification and Et2O extraction yielded 7.3 g. 4-acetyl-5-ethyl-2-methylpyridine (IV), b20 114-18°; picrate, m. 132-4°; oxime, m. 107°. Clemmensen reduction of 7.3 g. IV gave 4.3 g. 4,5-diethyl-2-methylpyridine (V), prepared by Kao and Robinson (C.A. 50, 5620b); styphnate, m. 155-6°. The residue from the working up contained 5-ethyl-4-(1-hydroxyethyl)-2-methylpyridine, b0.1 100-5° (picrate, m. 137-9°); reduction (HIP) of this base gave V. On refluxing 70 hrs. 4.3 g. V with 11 cc. BzH and 11 cc. Ac2O in 12 cc. xylene followed by acidification (17% HCl to Congo red), removal (steam distillation) of BzH, basification (NaOH), and CHCl3 extraction gave 1 g. unchanged V and 4.3 g. 4,5-diethyl-2-styrylpyridine (VI), picrate, m. 241-3° (decompose) (cf. K. and R., loc. cit.). Oxidation of 2 g. VI in Me2CO at 0° by the addition of 7 g. KMnO4 followed by 1 hr. stirring, removal and washing (Me2CO and H2O) of MnO2, and extraction of BzOH, gave on continuous Et2O extraction of the aqueous liquor at pH 4 0.6 g. 4,5-diethylpyridine-2-carboxylic acid (VII), m. 147-8°, λmaximum 2680 and 2300 A. (log ε 3.61 and 3.90 resp.), λmin. 2520 A. (log. ε 3.44), identical by mixed m.p. with acid of natural origin. Demethylation (Cu powder) of VII gave 4,5-diethylpyridine, identified as the picrate. VII (0.6 g.) on esterification (10 cc. EtOH and dry HCl at 0°, standing overnight and then refluxing for 2 hrs.) gave 0.6 g. Et ester (VIII), b3 140-5°; picrate, m. 88-90°. VIII (0.5 g.) with 5 cc. NH4OH (d. 0.880) 48 hrs. (room temperature) followed by 2 hrs. stirring yielded 2-carbamoyl-4,5-diethylpyridine (VIIIa), subliming at 100-20°/0.1 mm., m. 177-8°. Dehydration (1 cc. POCl3, reflux 2 hrs.) of 0.4 g. VIIIa gave on working up 0.2 g. 2-cyano-4,5-diethylpyridine, b20 150-60°, which (1.3 g.) in 75 cc. EtOH added with stirring to PrMgBr (from 0.6 g. Mg and 2.7 g. PrBr in 15 cc. Et2O), and the mixture refluxed 3 hrs. and decomposed (30 cc. saturated NH4Cl and 5 cc. concentrated HCl) afforded on basification and Et2O extraction 1.2 g. 2-butyryl-4,5-diethylpyridine (IX), b3 142-6°; picrate, m. 97-8°; phenylhydrazone picrate, m. 211-12°; p-methoxyphenylhydrazone picrate, m. 160-1°. On heating 0.334 g. IX with 0.18 g. PhNHNH2 in vacuo on a steam bath 2 hrs., the product, on solution in 20 cc. EtOH, cooling in ice, keeping at room temperature 1 hr. followed by refluxing 2 hrs., gave on evaporation, basification, and Et2O extraction 0.3 g. 2-(4,5-diethyl-2-pyridyl)-3-ethylindole (X), b0.4 200-10°, m. 110-1°, identical by mixed m.p. with alstyrine from alkaloidal degradation, λmaximum 3250 A. (log ε 4.36), and λmin. 2740 A. log ε 3.63; picrate, m. 218-21°; hydrochloride, softened at 190° and melted completely at 203°. As in the synthesis from VI above, starting from 4 g. ethyl 5-ethylpyridine-2-carboxylate there were obtained: 3 g. 2-carbamoyl-5-ethylpyridine, m. 147-8°; 1.7 g. 2-cyano-5-ethylpyridine, b20 132°; 1.3 g. 2-butyryl-5-ethylpyridine (XI) (p-methoxyphenylhydrazone picrate, m. 176-7°). XI with p-MeOC6H4NHNH2 yielded 3-ethyl-2-(5-ethyl-2-pyridyl)-5-methoxyindole (XII), m. 111-12°, λmaximum 3320 A. (log ε 4.49), λmin. 2720 A. (log ε 3.36); picrate, m. 201-3°. Similarly X with p-MeOC6H4NHNH2 gave 2-(4,5-diethyl-2-pyridyl)-3-ethyl-5-methoxyindole (XIII), b0.1 200-20°, m. 148°, λmaximum 3290 A. (log ε 4.43), λmin. 2730 A. (log ε 3.67); picrate, m. 225° (decomposition). Neither XII or XIII were identical with the degradation product from aricine (Goutarel, et al., C.A. 50, 5687g). The experimental process involved the reaction of 4-Bromo-5-ethyl-2-methylpyridine(cas: 98488-99-4).Recommanded Product: 98488-99-4

4-Bromo-5-ethyl-2-methylpyridine(cas:98488-99-4) belongs to pyridine-derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Recommanded Product: 98488-99-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem