Category: pyridine-derivatives

A common compound: 23056-33-9, name is 2-Chloro-4-methyl-5-nitropyridine,molecular formula is C6H5ClN2O2, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below., 23056-33-9

2-Chloro-4-methyl-5-nitropyridine (20.5 g, 119 mmol) was dissolved in concentrated sulfuric acid (200 ml), and chromium trioxide (40.0 g, 400 mmol) was added thereto, followed by stirring at 0 C. for 1 hour. Then, the temperature was gradually raised from 0 C. to room temperature, followed by stirring for 12 hours. The reaction solution was poured into ice-water (2000 ml), and the temperature was raised from 0 C. to room temperature. The precipitated solid was filtered and dried under reduced pressure to obtain the title compound (18 g, 750). [0144] 1H NMR (CD3OD, 400 MHz): delta 10.8 (1H, br, s), 9.13 (1H, s), 7.70 (1H, s)

With the rapid development of chemical substances, we look forward to future research findings about 23056-33-9.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

2016-99-1, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 2016-99-1 as follows.

2,2,6,6-tetramethylpiperidine (10 ml, 59.3 mmol, Acros Organics) was added to 2,6- dibromoisonicotinic acid (2004 mg, 7.13 mmol, Fluorochem) and (S)-3-ethylmorpholine hydrochloride (1300 mg, 8.57 mmol, Manchester Organics). The vial containing reaction mixture was sealed, heated to 200 C and stirred at 200 C for 16 h. The reaction mixture was partitioned between DCM (lOOmL) and water (150ml_) acidified with 2M HCI. The organic layer was separated and extracted with DCM (50 ml_). The organic layers were combined, dried over a hydrophobic frit, and concentrated under reduced pressure. The residue was purified by reverse phase HPLC with a gradient of 30-85% acetonitrile + 0.1% formic acid. Concentration in vacuo afforded (S)-2-bromo-6-(3- ethylmorpholino)isonicotinic acid (1268 mg, 4.02 mmol, 56.4% yield) as a brown solid. LCMS (System B, UV, ESI): Rt = 1.14 min, [M+H]+ 315 + 317

The chemical industry reduces the impact on the environment during synthesis 2016-99-1, I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BRAVI, Gianpaolo; HOBBS, Heather; INGLIS, Graham George Adam; NICOLLE, Simon; PEACE, Simon; (138 pag.)WO2019/115640; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

100-26-5, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 100-26-5, name is 2,5-Pyridinedicarboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

fac-[NEt4]2[Re(CO)3(Br)3] (100.0 mg, 0.130 mmol) was dissolved in water at pH 2.2. Silver nitrate (66.0 mg, 0.389 mmol) was added to the solution and stirred for 24 h at room temperature. After the reaction mixture was filtered (AgBr), 2,5-pyridine dicarboxylic acid(22.0 mg, 0.133 mmol) was added to the solution and stirred under N2 at room temperature for 48 h. The mixture was filtered and the filtrate (pH 2.5) was dried in vacuo. Yield: 55.4 mg, 94 %. IR (KBr,cm-1): mCO = 1899, 2017, 2043. 1H NMR (CD3COCD3): delta = 7.93 (d,1H, J = 8.1 Hz), 8.58 (dd, 1H, J = 1.8 Hz, 8.1 Hz), 9.47 (s, 1H). 13CNMR (CD3COCD3): delta = 128.7, 132.9, 142.7, 151.6, 154.5, 164.5, 178.0, 195.0, 197.6, 198.1. HPLC: 17.84 min. Anal. Calc. C, 26.43;H, 1.33; N, 3.08. Found: C, 26.45; H, 1.30; N, 3.12%.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 100-26-5, 2,5-Pyridinedicarboxylic acid.

Reference:
Article; Schutte-Smith; Visser; Polyhedron; vol. 89; (2015); p. 122 – 128;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

89878-14-8, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 89878-14-8, name is 3-(Diethylboryl)pyridine. A new synthetic method of this compound is introduced below.

A 500 mL Parr bottle was charged with 2.0 g of 10% palladium on carbon (50% water) and covered with 50 mL ethanol. 2-methyl-5-nitroanisole (10.0 g, 59.8 mmol) was dissolved in 100 mL ethanol and added to the catalyst suspension. The reaction was hydrogenated at 50 psi for 3 h. The catalyst was filtered through a celite plug. The filter cake was washed with 150 mL ethanol and the filtrated concentrated under reduced pressure to yield 8.05g (98%) of 5-amino-2-methylanisole as a clear oil. ‘H NMR (400 MHz, CDC13) 8 6. 90 (d, 1 H), 6.23 (m, 2H), 3.78 (s, 3H), 2.11 (s, 3H). 5-amino-2-methylanisole (8.05 g, 58.7 mmol) was dissolved in 244 mL water and 8.1 mL concentrated H2SO4 and cooled to 0C. NAN02 (4.86 g, 70.4 mmol) in 61 mL water was added dropwise with stirring. Reaction was stirred 30 minutes at 0C. Urea (0.70 g, 11.7 mmol) was added and stirring continued for an additional 30 minutes. The pale yellow solution was transferred to a dropping funnel and added slowly to a stirred solution of potassium iodide (19.48 g, 117.4 mmol) in 122 mL water. The solution was stirred at ambient temperature for 1 h after completion of the addition. The reaction was extracted with diethyl ether (3 x 300 mL). The organic extracts were combined and washed with 1 M Na2S203 (2 x 200 mL), dried over NA2SO4, filtered and concentrated under reduced pressure to yield 9.60 g (66%) of 5- iodo-2-methyl anisole as a brown oil. 1H NMR (400 MHz, CDC13) 8 7.19 (dd, 1H), 7.10 (d, 1H), 6.86 (t, 1H), 3.81 (s, 3H), 2.15 (s, 3H). 5-iodo-2-methyl anisole (9.60 g, 38.70 mmol) and diethyl- (3-pyridyl) borane (5.70 g, 38.70 mmol) were dissolved in 60 mL tetrahydrofuran in a 250 mL round bottom flask equipped with a magnetic stirrer. Sodium carbonate (8.20 g, 77.40 mmol) and 30 mL water were added followed by tetrakis (triphenylphosphine) palladium (0) (0.90g, 0.77 mmol) and 15 mL ethanol. The mixture was heated at reflux for 24 h under nitrogen then cooled to ambient temperature. The mixture was diluted with 200 mL water and extracted with diethyl ether (2 x 200 mL). The organic phases were combined and extracted with’N HCI (3 x 150 mL). The acidic extractions were combined and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with diethyl ether (3 x 150 mL) and the extracts were combined and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 7. 71G (99%) of 2-methyl-5- (3-pyridyl)- anisole as a brown oil. MS (LC-MS) 200.1 (M + H) +. ‘H NMR (400 MHz, CDGI3) 8 8.87 (s, 1 H), 8.60 (d, 1 H), 8.03 (dd, 1 H), 7.50 (m, 1 H), 7.25 (d, 1H), 7.08 (d, 1 H), 7.00 (s, 1 H), 3.92 (s, 3H), 2.27 (s, 3H). A 500 mL L hydrogenation vessel was charged with 0.77 g platinum (II) oxide and purged with nitrogen. 2-methyl-5- (3-pyridyl)-anisole (7.71 g, 38.7 mmol) was added as a solution in 150 mL acetic acid. The suspension was hydrogenated at 45 psi for 18 h. The catalyst was filtered through celite and the filter plug was washed with 200 mL acetic acid. The filtrate was concentrated under reduced pressure. The resultant oil was taken up in 300 mL water and made basic with 5N aqueous sodium hydroxide. This basic layer was extracted with ethyl acetate (2 x 300 mL) and the extracts were combined and dried over anhydrous sodium sulfate,,. filtered and concentrated under reduced pressure. The resultant oil was taken up in 300 mL hot ethanol. L- (+)-tartaric acid (5.81 g, 38.7 mmol) in 50 mL hot ethanol was added into the ethanol solution and was allowed to stir at ambient temperature for 24 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5% H2O/ETHANOL (200 mL) to yield 4.88 g (35%) of 5- (3-PIPERIDINYL)-2- methylanisole-L-tartaric acid salt as a white solid. The mother liquors were combined and concentrated under reduced pressure. The resultant oil was taken up in 500 mL diethyl ether and washed with 300 mL saturated aqueous NAHCO3. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resultant oil was taken up in 200 mL hot ethanol. D- (-)-tartaric acid (3.75 g, 25.0 mmol) in 50 mL hot ethanol was added and was allowed to stir at ambient temperature for 48 h, forming a white precipitate that was collected by filtration. The white solid was recrystallized from hot 5% H20/ETHANOL (300 mL) to yield 5.36 g (39%) of 5- (3-PIPERIDINYL)-2-METHYLANISOLE-D-TARTARIC acid salt as a white solid. ‘H NMR (400 MHz, DMSOd6) 8 7.06 (d, 1 H), 6.82 (d, 1 H), 6.71 (dd, 1 H), 3.87 (s, 2H), 3.77 (s, 3H), 3.27 (m, 2H), 2.97 (t, 1H), 2.86 (q, 2H), 2.09 (s, 3H), 1.85 (d, 2H), 1.69 (m, 2H). 3- (3-methoxy-4-methylphenyl)-1 H-piperidine-L-tartaric acid salt (4.88 g, 13.73 mmol) was slowly dissolved in hydrobromic acid (50 mL) and the resulting mixture heated at 140 C for 2 h. After cooling to ambient temperature, the hydrobromic acid and water were distilled off and the resulting brown oil was azeotroped with to…

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 89878-14-8, 3-(Diethylboryl)pyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER PRODUCTS INC.; WO2004/48334; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1122-54-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 1122-54-9 as follows.

4-Bromoacetyl-pyridine, HBr salt; Dibromine (17.2g, 108 mmol) was added dropwise to a cold (0C) solution of 4-acetyl- pyridine (12 g, 99 mmol) in acetic acid containing 33% of HBr (165 mL) under vigourous stirring. The vigorously stirred mixture was warmed to 40C for 2h and then to 75C. After 2h at 75C, the mixture was cooled and diluted with ether (400 mL) to precipitate the product. which was recovered by filtration and washed with ether and acetone to give white crystals (100%). This material may be recrystallised from methanol and ether.

The chemical industry reduces the impact on the environment during synthesis 1122-54-9, I believe this compound will play a more active role in future production and life.

Reference:
Patent; AB SCIENCE; WO2005/73225; (2005); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

586-95-8, Adding a certain compound to certain chemical reactions, such as: 586-95-8, 4-Pyridinemethanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, 586-95-8, blongs to pyridine-derivatives compound.

To a solution of pyridin-4-ylmethanol (25.7 g, 0.24 mol) and imidazole (19.8 g, 0.29 mol) in dry DMF (300 mL) and dry DCM (33 mL) under nitrogen atmosphere was added TBDMSCl (42.6 g, 0.29 mol). The solution was stirred for 18 h under which time a precipitate formed. The reaction mixture was concentrated by removal of volatiles (about 100 mL) followed by addition of water (500 mL). The resulting mixture was extracted with 1:1 heptane:EtOAc (200 mL¡Á3). The combined organic phases were washed with brine (¡Á2), dried (MgSO4), filtered and evaporated to yield 4-((tert-butyldimethylsilyloxy)-methyl)pyridine (51.70 g, 98%) as an oil. 1H NMR (600 MHz, cdcl3) delta -0.01 (s, 6H), 0.82 (s, 9H), 4.63 (s, 2H), 7.14 (m, 2H), 8.43 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,586-95-8, its application will become more common.

Reference:
Patent; AstraZeneca AB; US2010/261755; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

13472-85-0, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 13472-85-0, name is 5-Bromo-2-methoxypyridine. A new synthetic method of this compound is introduced below.

Step j: 2-methoxy-5-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Compound R-3-2) A mixture of compound 303 (55 g, 0.29 mol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (90 g, 0.35 mol), potassium acetate (57 g, 0.58 mol) and bis(triphenylphosphine)palladium(II) chloride (2.2 g, 3 mmol) in anhydrous dioxane (500 mL) was heated at 108 C. under N2 atmosphere overnight. The reaction mixture was concentrated and purified by column chromatography eluted with hexanes/ethyl acetate to afford title compound R-3-2 (58 g, 84%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,13472-85-0, 5-Bromo-2-methoxypyridine, and friends who are interested can also refer to it.

Reference:
Patent; Curis, Inc.; Cai, Xiong; Zhai, Haixiao; Lai, Chengjung; Qian, Changgeng; Bao, Rudi; (50 pag.)US9249156; (2016); B2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1122-54-9, A common compound: 1122-54-9, name is 4-Acetylpyridine,molecular formula is C7H7NO, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Preparation of 4-Bromoacetylpyridine, HBr saltHBrBromine (24 g, 150 mmol) in 4 mL of 45% HBr was added drop wise under vigorous stirring to a solution at 70C of 4-acetyl-pyridine (18 g, 148 mmol) in acetic acid containing 45% of HBr (165 mL). The vigorously stirred mixture was kept at 700C for 3h. The mixture was cooled and the precipitate collected by filtration and washed with petroleum ether(40-65C)/methanol (1/1, 100 mL) to give 35.8 g of a white crystals of (85%).

With the rapid development of chemical substances, we look forward to future research findings about 1122-54-9.

Reference:
Patent; AB SCIENCE; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE(CNRS); INSTITUT CURIE; WO2006/106437; (2006); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6443-85-2, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 6443-85-2, name is 2-(Pyridin-3-yl)acetonitrile. This compound has unique chemical properties. The synthetic route is as follows.

34.1.2 Synthesis of 3-cyano-3-(pyrid-3-yl)pentanedioic acid diethyl ester Combine 3-pyridineacetonitrile (25 g, 212 mmol) and tetrahydrofuran (200 mL). Cool to about -70 C. using a dry-ice/acetone bath. Add dropwise, a solution of sodium bis(trimethylsilyl)amide (435 mL, 1 M in tetrahydrofuran, 435 mmol) while maintaining the reaction temperature below about -68 C. When the addition is complete, warm the reaction mixture to ambient temperature and allow to stir for 1 hour. Transfer the above solution via cannula into a cooled (-5 C.) solution of ethyl bromoacetate (84.5 mL, 762 mmol) in tetrahydrofuran (500 mL) at such a rate that the temperature of the reaction mixture does not rise above about 15 C. Allow to stir at ambient temperature. After 18 hours, quench with saturated aqueous solution of ammonium chloride and evaporate in vacuo to remove most of the tetrahydrofuran. Extract the evaporated reaction mixture twice with diethyl ether. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluding with 1/1 ethyl acetate/hexane to give the title compound.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 6443-85-2, 2-(Pyridin-3-yl)acetonitrile.

Reference:
Patent; Aventis Pharmaceuticals Inc.; US6194406; (2001); B1;; ; Patent; Aventis Pharmaceuticals Inc.; US6423704; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

6635-90-1, A common compound: 6635-90-1, name is 2-Methoxy-4-methyl-5-nitropyridine,molecular formula is C7H8N2O3, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

A solution of 2-methoxy-4-methyl-5-nitropyridine (4.30 g, 25.57 mmol) and dimethylformamide dimethylacetal (35 ml) was heated at reflux under nitrogen for 40 hours. Ethyl acetate was added to this solution (150 ml), and this mixture was washed with water (150 ml). The aqueous extract was back-extracted with ethyl acetate (100 ml), and the organic extracts were combined, dried (Na2 O4), and evaporated under reduced pressure to yield a purple solid. The solid was dissolved in absolute ethanol (200 ml), and 5% palladium on carbon (3.0 g) was added to this solution which was shaken under a hydrogen atmosphere (3 atm) for 3 hours. The resultant reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. Flash chromatography of the residue yielded compound 9 (2.05 g, 13.84 mmol, 54% last step, 50% overall) as a white crystalline solid: mp, 123-124 C.; IR (KBr) 1625, 1580, 1490, 1460, 1320, 1150 cm-1; 1 H NMR (DMSO-d6) delta 11.28 (br s, 1H), 8.37 (s, 1H), 7.57 (t, J=2.8 Hz, 1H), 6.86 (s, 1H), 6.33 (br m, 1H), 3.82 (s, 3H); 13 C NMR (DMSO-d6) delta 157.2, 136.4, 131.5, 130.7, 130.0, 99.6, 96.8, 53.4; LRMS (m/z, relative intensity) 149 (20), 148 (M+, 98), 147 (100), 119 (46), 118 (79), 117 (26), 105 (31), 91 (15), 70 (16); HRMS calculated for C8 H8 N2 O:148.0657, found: 148.0613.

With the rapid development of chemical substances, we look forward to future research findings about 6635-90-1.

Reference:
Patent; Pfizer Inc.; US5051412; (1991); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem