Day: November 10, 2020

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. 769-27-7, name is 6-Amino-2,4-dimethylnicotinonitrile. This compound has unique chemical properties. The synthetic route is as follows. 769-27-7

A suspension of 6-amino-3-cyano-2,4-dimethylpyridine (0.1 g, 0.68 mmol) in CH2Cl2 (1 mL) was added to a vigorously stirred mixture of CaCO3 (0.41 g, 4.11 mmol) in a 1:2 water:CH2Cl2 mixture (9 mL total) at room temp. The reaction mixture was cooled to 0 C. and thiophosgene (0.09 g, 0.78 mmol) was added dropwise. The resulting mixture was allowed to warm to room temp and was stirred overnight. The resulting aqueous layer was back-extracted with CH2Cl2 (3¡Á10 mL). The combined organic layers were washed with water (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by chromatography (SiO2, 10% EtOAc/hex) to give 2,4-dimethyl-3-cyano-6-pyridyl isothiocyanate (0.12 g, 91%): CI-MS m/z 190 ((M+H)+)

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, 769-27-7, 6-Amino-2,4-dimethylnicotinonitrile.

Reference:
Patent; Bayer Corporation; US6353006; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

97483-77-7, Adding some certain compound to certain chemical reactions, such as: 97483-77-7, name is 5-Bromopicolinonitrile,molecular formula is C6H3BrN2, 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 97483-77-7.

PREPARATION 108[1-(5-Bromo-pyridin-2-yl)-ethyl]-carbamic acid tert-butyl esterTo a stirred solution of 5-bromo-pyridine-2-carbonitrile (1 g, 5.46 mmol) in dry THF (10 mL) was added dropwise MeMgBr (2.03 mL, 6.09 mmol,3M in THF) at -20 C under N2 atmosphere. After the addition, the reaction mixture was stirred at room temperature for 30 mins. The suspension was then treated with methanol (20 mL) and NaBH (0.4 g, 13.3 mmol). The reaction was stirred at room temperature for 10 hrs and then poured into H20 (10 mL) and aqueous NaOH (2M, 10 mL), extracted with EtOAc (50 mL chi 2). The combined organic layers were washed with brine (50 mL chi 3), dried over Na2S0 and concentrated in vacuum. The residue was purified by a silica gel columnchromatography (petroleum: EtOAc 3:1 ) to give 1-(5-bromo-pyridin-2-yl)-ethylamine (0.65 g, 59%) as a yellow liquid. To a solution of 1-(5-bromo-pyridin-2-yl)-ethylamine (500 mg, 2.48 mmol) and E_3N (300 mg, 2.98 mmol) in DCM (10 ml_) was added Boc20 (650 mg, 2.98 mmol) at room temperature. After the addition, the reaction mixture was stirred at room temperature for 5 hrs. TLC (petroleum ether: EtOAc 5:1 ) indicated the reaction was completed. Then the mixture was poured into brine (10 ml_) and extracted with with DCM (50 ml_ 3), washed with brine (10 ml_ chi 3), dried over Na2SO4, concentrated in vacuum to give the residue, which was purified by Biotage (petroleum ether/EtOAc 3:1 , Rf~ 0.6) to give the title compound (450 mg, 60%) as a yellow solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 97483-77-7.

Reference:
Patent; PFIZER INC.; BUNNAGE, Mark, Edward; COOK, Andrew, Simon; CUI, Jingrong, Jean; DACK, Kevin, Neil; DEAL, Judith, Gail; GU, Danlin; HE, Mingying; JOHNSON, Patrick, Stephen; JOHNSON, Ted, William; LE, Phuong, Thi, Quy; PALMER, Cynthia, Louise; SHEN, Hong; WO2011/138751; (2011); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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

A solution of 2-chloro-4-methyl-5-nitropyridine (5.13 g, 29.73 mmol) in concentrated sulfuric acid (42 mL) was cooled to 0 C., and chromium trioxide (9.81 g, 98.1 mmol) was added. The mixture was stirred at 0 C. for 1 hour and then warmed to room temperature, with an oil bubbler attached, for overnight stirring. The reaction mixture was poured onto ice (300 ml) and diluted with water (150 ml). The mixture was warmed to room temperature, and the solid was filtered and then dried under vacuum to yield 2-chloro-5-nitroisonicotinic acid. To a stirred solution of the above material (5.3 g, 26.17 mmol) in methanol (50 ml) was added chloroform (200 ml). TMS-diazomethane as a solution in hexane (2M) was added dropwise until the color of the reaction mixture remained yellow (20 mL). The residual TMS-diazomethane was quenched by addition of acetic acid, and the solvent was removed under reduced pressure. The oily residue was subjected to silica gel chromatography eluted with 50-70% ethyl acetate in hexane to provide methyl 2-chloro-5-nitroisonicotinate. A solution of the above material (5.66 g, 26.13 mmol), methyl 4′-(aminomethyl)-3,3′-difluorobiphenyl-2-carboxylate (7.971 g, 28.75 mmol, prepared according to procedures described in WO 03/066577), and triethylamine (3.97 g, 39.20 mmol) in methanol (100 ml) was stirred at room temperature overnight. The solution was then heated at 60 C. for 4 hours and cooled to ambient temperature for continued stirring over the weekend. Solvent was removed, and the residue was subjected to silica gel chromatography eluted with 25-50% ethyl acetate in hexane to provide methyl 2-({[3,3′-difluoro-2′-(methoxycarbonyl)biphenyl-4-yl]methyl}amino)-5-nitroisonicotinate as a yellow solid. A solution of the above material (9.3 g, 20.33 mmol) in methanol (330 ml) was purged with nitrogen, and 10% Pd/C catalyst (1 g) was added. The reaction vessel was again purged with nitrogen and then with hydrogen from a balloon. After 23 hours of stirring under hydrogen, nitrogen was bubbled through the solution for 10 minutes prior to filtration through a celite pad. The filtrate was concentrated under reduced pressure to provide methyl 5-amino-2-({[3,3′-difluoro-2′-(methoxycarbonyl)biphenyl-4-yl]methyl}amino)isonicotinate. Into a solution of the above material (8.45 g, 19.77 mmol) in THF (440 ml) at 0 C. were added hypophosphorous acid (50% solution in water, 110 ml) and sodium nitrite (2.73 g, 39.54 mmol). After 10 minutes of stirring, a catalytic amount of copper (I) oxide was added every 30 minutes for 7.5 hours. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate and brine, then dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography eluted with 20-40% ethyl acetate in hexane to provide methyl 2-({[3,3′-difluoro-2′-(methoxycarbonyl)biphenyl-4-yl]methyl}amino)isonicotinate. To a stirred solution of the above material (3.96 g, 9.60 mmol) in methanol (85 ml) was added 1N NaOH (11.5 ml), and the solution was heated at 40 C. for 3.5 hours. Solvent was removed under reduced pressure prior to dilution with water. The aqueous solution was washed with diethyl ether twice, and the residual diethyl ether in the aqueous solution was removed under reduced pressure. The aqueous solution was neutralized by addition of 1N HCl (11.5 ml), and the resulting thick suspension was heated (70 C.) and then slowly cooled to ambient temperature before being cooled to 0 C. for 30 minutes. The solid was filtered and dried under vacuum, providing the title compound as a white solid. LRMS (ES, M+H+): 399. 1H NMR (CD3OD, 400 MHz) delta 8.04 (d, J=5.6 Hz, 1H), 7.55 (m, 1H), 7.44 (t, J=8 Hz, 1H), 7.23 (m, 3H), 7.10 (m, 3H), 4.65 (s, 2H), 3.66 (s, 3H).

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

Reference:
Patent; Wood, Michael R.; Bock, Mark G.; Books, Kathy M.; Freidinger, Roger M.; Kim, June J.; US2006/122236; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

1721-26-2, 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 1721-26-2, name is Ethyl 2-methylnicotinate. This compound has unique chemical properties. The synthetic route is as follows.

(a) Ethyl 6-(tert-butyl)-2-methylpyridine-3-carboxylate. Analogous to the procedure used to prepare Example 44, step (a), ethyl 2-methylnicotinate (8.3 g, 50 mmol, Aldrich), trimethylacetic acid (26 g, 250 mmol, Aldrich), silver nitrate (1.7 g, 10 mmol, Aldrich), 10percent aq. sulfuric acid (50 mL) and ammonium persulfate (23 g, 100 mmol, Aldrich) provided, after purification by silica gel chromatography (80:20 hexane:EtOAc), the title product. MS (ESI, pos. ion) m/z: 222 (M+1).

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 1721-26-2, Ethyl 2-methylnicotinate.

Reference:
Patent; Bo, Yunxin Y.; Chakrabarti, Partha P.; Chen, Ning; Doherty, Elizabeth M.; Fotsch, Christopher H.; Han, Nianhe; Kelly, Michael G.; Liu, Qingyian; Norman, Mark Henry; Ognyanov, Vassil I.; Wang, Xianghong; Zhu, Jiawang; US2003/195201; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

109-04-6, 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. 109-04-6, name is 2-Bromopyridine. A new synthetic method of this compound is introduced below.

Example 1 was repeated using anhydrous zinc bromide (22.5 g, 0.10 mol) instead of zinc chloride. The yield in moles of 4-(2′-pyridyl)benzaldehyde relative to the 2-bromopyridine added was 93%, the turnover of the catalyst (Pd) 1744.

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. 109-04-6, 2-Bromopyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Euticals Prime European Therapeutical SpA; US6765097; (2004); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The common heterocyclic compound, 462-08-8, name is Pyridin-3-amine, molecular formula is C5H6N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 462-08-8

In the three bottle,3-aminopyridine (20.0 g, 212.5 mmol),4-Dimethylaminopyridine (4-DMAP) (0.3 g, 2.1 mmol)And pyridine (33.6 g, 425.0 mmol) dissolved in anhydrous dichloromethane (200 mL),Pivaloyl chloride (28.2 g, 233.7 mmol) was slowly added dropwise in an ice bath.0 C reaction 2h.After the reaction was completed, the reaction solution was poured into ice water, quenched with 1N hydrochloric acid, extracted with dichloromethane (250 mL¡Á3), and the organic phase was collected and washed with saturated brine (200 mL¡Á1).The solvent was evaporated under reduced pressure to give 3-pivalamidopyridine (36.2 g).Yield 95.5%.

The synthetic route of 462-08-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guizhou University; Liu Li; Huang Zhuyan; Yue Yi; (8 pag.)CN107382839; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

5470-18-8 ,Some common heterocyclic compound, 5470-18-8, molecular formula is C5H3ClN2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Methylamine (33% in EtOH) (1 10 mL, 883 mmol) was placed in a 500 mL three necked round bottom flask. It was cooled to 0 C using ice bath. 2-chloro-3-nitropyridine (20 g, 126 mmol) was added to the above solution in portions as this is an exothermic reaction. After the addition was complete the reaction mixture was stirred for 2 h at 0 C and later 1 h at room temperature. Solvent was concentrated and residue was taken in 500 mL of water and extracted with EtOAc 3 x 150 mL. Combine organic layer was dried over Na2SC”4, filtered and concentrated to give a bright orangish yellow solid(19 g , 98.5%).

According to the analysis of related databases, 5470-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSAL DISPLAY CORPORATION; WU, Yonggang; XIA, Chuanjun; FIORDELISO, James; LAYEK, Suman; ALLEYNE, Bert; DYATKIN, Alexey, Borisovich; ANSARI, Scott; BEERS, Scott; BARRON, Ed; BROOKS, Jason; WO2012/121936; (2012); A2;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 553-26-4, 4,4′-Bipyridine, 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, 553-26-4, blongs to pyridine-derivatives compound. 553-26-4

A mixture of 4,4′-bipyridyl (20 g) in water (330 mL) was hydrogenated at 5 atmospheres pressure and at 50 C. over 5% Rh-C catalyst (5.0 g). The uptake of hydrogen gas was continued until the thermatical amount of hydrogen had been absorbed. After cooling, the catalyst was removed by filtration through celite. The water was evaporated and the residue azeotroped with toluene (2¡Á100 mL). The residue was purified by chromatography on neutral alumina using a mixture of dichloromethane-methanol (98:2) as eluent to give, as a cream-coloured solid, 4-(4-pyridyl)piperazine (11.4 g): m.p. 82-84 C.: NMR (CDCl3); 1.57-1.70(qd, 2H), 1.82(m, 2h), 2.53-2.63(ttt, 1H), 2.68-2.80 (td, 2H), 3.20 (d, 2H), 7.12(d, 2H), 8.52(d, 2H); EI-MS m/z 163 (M+H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,553-26-4, its application will become more common.

Reference:
Patent; Zeneca Limited; US6391880; (2002); B1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 6419-36-9, name is 2-(Pyridin-3-yl)acetic acid hydrochloride. A new synthetic method of this compound is introduced below., 6419-36-9

Example C2 Synthesis of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic Acid In a 100 ml rounded bottom, three necked flask equipped with a magnetic stirrer, a thermometer, a reflux condenser and a compensated-pressure dropping funnel were charged: 1.00 g (5.76¡¤10-3 mol) of 3-pyridyl acetic acid hydrochloride, 1.46 g (1.78¡¤10-2 mol) of phosphonic acid, 3.01 g (1.72¡¤10-2 mol) of methanesulfonic anhydride and 7.2 ml of toluene. 1.22 g of PCl5 was steeply added at room temperature. Exothermy, gas evolution and foaming was observed. The mixture was then heated up to 95 C. At about 40 C., formation of two well defined liquid phases were observed. The mixture was kept overnight at 95 C. No stirring problems arose. The mixture was then let to cool down to 80 C. at which point 7.2 ml of water were added dropwise (exothermy was observed). The mixture was stirred at 80 C. for 15 minutes and then let to cool down to room temperature. The aqueous layer was decanted and heated to 95 C. for 5.5 h and let to cool down to room temperature, at which point 7.2 ml of ethanol were added. The resulting mixture was cooled down to 5 C., stirred for 1 h and filtered. The solid washed with ethanol and dried at 40 C. in a vacuum oven until constant weight. 1.01 g of 3-pyridyl-1-hydroxyethylidene-1,1-bisphosphonic acid monohydrate are obtained (Yield: 58.23%) Chromatographic purity: 98.327% (area percent)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,6419-36-9, 2-(Pyridin-3-yl)acetic acid hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Serrano, Jordi Puig; Illado, Jordi Bosch; US2008/194525; (2008); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

69045-84-7, Adding a certain compound to certain chemical reactions, such as: 69045-84-7, 2,3-Dichloro-5-(trifluoromethyl)pyridine, 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, 69045-84-7, blongs to pyridine-derivatives compound.

Step A Synthesis of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine To a solution of 60 mL of hydrazine monohydrate in 380 mL of ethanol was added 81 g (0.38 mole) of 2,3-dichloro-5-trifluoromethylpyridine during a period of 25 minutes. At the end of the addition the temperature had risen to 37 C. This mixture was heated to reflux and maintained at reflux for approximately 15 hours. The solvent was evaporated under reduced pressure, leaving a wet slurry that was immediately recrystallized from boiling ethanol/water (5:2). The mixture was cooled to 20 C. and then filtered. The filter cake was air-dried, yielding approximately 60 g of 3-chloro-5-trifluoromethylpyrid-2-ylhydrazine. The NMR spectrum was consistent with the assigned structure. This reaction was repeated to obtain additional material for subsequent reactions.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,69045-84-7, its application will become more common.

Reference:
Patent; FMC Corporation; US5321002; (1994); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem