Category: 18368-64-4

Electric Literature of 18368-64-4 ,Some common heterocyclic compound, 18368-64-4, molecular formula is C6H6ClN, 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.

2-Chloro-5-methylpyridine (10.03 g, 79 mmol), (3-chloro-4-methylphenyl)boronic acid (13.4 g, 79 mmol), and potassium carbonate (21.74 g, 157 mmol) were dissolved in the mixture of DME (150 ml) and water (20 ml) under nitrogen to give a colorless suspension. Pd(PPh3)4(0.909 g, 0.786 mmol) was added to the reaction mixture, then the reaction mixture was degassed and heated to 95° C. for 12 hrs. It was then cooled down to room temperature, separated organic phase and evaporated. The residue was subjected to column chromatography on silica gel column, eluted with heptanes/THF 9/1 (v/v), providing after crystallization from heptanes 10 g of 2-(3-chloro-4-methylphenyl)-5-methylpyridine (58percent yield) of white solid.

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. 18368-64-4, 2-Chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Worldwide Show Corporation; Cai Ruiyi; Ji Zhiqiang; Ya Likexi·baolisuoweiqi·diyatejin; Xia Chuanjun; Lin Chun; Zeng Lichang; Wo Erte·yegeer; (191 pag.)CN107522748; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-64-4 ,Some common heterocyclic compound, 18368-64-4, molecular formula is C6H6ClN, 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.

2-Chloro-5-methylpyridine (10.03 g, 79 mmol), (3-chloro-4-methylphenyl)boronic acid (13.4 g, 79 mmol), and potassium carbonate (21.74 g, 157 mmol) were dissolved in the mixture of DME (150 ml) and water (20 ml) under nitrogen to give a colorless suspension. Pd(PPh3)4(0.909 g, 0.786 mmol) was added to the reaction mixture, then the reaction mixture was degassed and heated to 95° C. for 12 hrs. It was then cooled down to room temperature, separated organic phase and evaporated. The residue was subjected to column chromatography on silica gel column, eluted with heptanes/THF 9/1 (v/v), providing after crystallization from heptanes 10 g of 2-(3-chloro-4-methylphenyl)-5-methylpyridine (58percent yield) of white solid.

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. 18368-64-4, 2-Chloro-5-methylpyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Worldwide Show Corporation; Cai Ruiyi; Ji Zhiqiang; Ya Likexi·baolisuoweiqi·diyatejin; Xia Chuanjun; Lin Chun; Zeng Lichang; Wo Erte·yegeer; (191 pag.)CN107522748; (2017); A;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-64-4, 2-Chloro-5-methylpyridine, 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, Formula: C6H6ClN, blongs to pyridine-derivatives compound. Formula: C6H6ClN

Triphenylphosphine (430 mg, 1 .64 mmol) was added to a solution of 2-chloro-5- fluorophenol (200 mg, 1 .37 mmol) in tetrahydrofuran (2 mL). The reaction mixture was cooled to 0 °C, and (c/s)-methyl 3-hydroxycyclobutanecarboxylate (213 mg, 1 .64 mmol) was added, followed by DIAD (0.32 mL, 1 .6 mmol). After 10 min, the reaction mixture was warmed to room temperature, stirred for 3 days, and diluted with water and EtOAc. The mixture was partitioned, and the aqueous layer was extracted with EtOAc. The organic layer was washed with water, dried over sodium sulfate, filtered, and concentrated. The residue was purified on silica gel eluting with a 10percent-50percent EtOAc-heptane gradient to give the title compound (264 mg, 64percent) as a yellow oil. 1H NMR (400 MHz, CDCI3) delta 2.50-2.61 (m, 2 H), 2.78 (ddd, J = 14, 7, 4 Hz, 2 H), 3.18-3.28 (m, 1 H), 3.76 (s, 3 H), 4.91 (quin, J = 7 Hz, 1 H), 6.49 (dd, J = 10, 3 Hz, 1 H), 6.63 (td, J = 8, 3 Hz, 1 H), 7.30 (dd, J = 9, 6 Hz, 1 H); LC-MS (LC-ES) M+H = 259, 261 (CI pattern).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; DEATON, David Norman; GUO, Yu; HANCOCK, Ashley Paul; SCHULTE, Christie; SHEARER, Barry George; SMITH, Emilie Despagnet; STEWART, Eugene L.; THOMSON, Stephen Andrew; (556 pag.)WO2018/69863; (2018); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-64-4, 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. 18368-64-4, name is 2-Chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

Fourth Step Production of methyl 3-(5-picoline-2-yl)aminosalicylate; Cesium carbonate (415 g), palladium acetate (8.8 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (25 g), methyl 3-amino-2-(2-methoxyethoxy)methyloxybenzoate (200 g) obtained in the preceding step, and 2-chloro-5-picoline (103 g) were added to toluene (1 L) in this order and stirred at 100° C. for 2 days. The reaction solution was filtered, and the filtrate was concentrated. Methanol (500 mL) and 6 N hydrochloric acid (200 mL) were added to the residue, and the mixture was refluxed and stirred for 0.5 hour. Active charcoal (25 g) was added to the reaction solution, and the mixture was stirred for 1 hour and then filtered. 1 N potassium citrate (2 L) was added to the filtrate, and the precipitated crystal was collected by filtration (218 g). The crystal collected by filtration was dissolved in ethyl acetate (1 L) and supplemented with silica gel (100 g), and the mixture was stirred at room temperature and then filtered. The filtrate was concentrated. The residue was recrystallized with acetone:water (2:1) (2 L), and the crystal was filtered and dried to obtain the title compound (128 g). (400 MHz, DMSO-d6): 2.18 (s, 3H), 3.92 (s, 3H), 6.89 (t, J=8.0 Hz, 1H), 7.04 (d, J=8.6 Hz, 1H), 7.35 (dd, J=7.9, 1.5 Hz, 1H), 7.42 (dd, J=8.4, 2.4 Hz, 1H), 7.98 (s, 1H), 8.19 (s, 1H), 8.48 (dd, J=8.2, 1.5 Hz, 1H), 11.30 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; Japan Tobacco Inc.; US2007/149517; (2007); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

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. 18368-64-4, name is 2-Chloro-5-methylpyridine. This compound has unique chemical properties. The synthetic route is as follows. Quality Control of 2-Chloro-5-methylpyridine

In a 1000 mL flask 450 g of chlorobenzene, 100 g of 2-chloro-5-methylpyridine and 3 g of cobalt acetate were added with stirring. The temperature of the heating system was raised to 80° C and the flow rate of oxygen was controlled at 0.4 L / Min and under these conditions the reaction was carried out for 4 hours. After completion of the reaction, the system was cooled to room temperature, filtered and dried to give 119 g of a mixture of 6-chloronicotinic acid and cobalt acetate. The above resulting mixed crude product was placed in a 1000 mL flask, then added 600 g of recrystallized solvent methanol, stirring heated to reflux until all the crude 6 – chloro nicotinic acid was dissolved, after 5 min of incubation, the system slowly cooled to 5°C, white crystal was precipitated, the stirring was continued for 1 hour while maintaining the internal temperature , then carried out flirtation , the filter cake was washed once with a small amount of cooled methanol and obtained product was dried at 80°C for 4 hours to obtain 98.5 g of 6-chloronicotinic acid, Purity 99. 52percent (HPLC), yield 79.7percent( Do not count the remaining product in the mother liquor, followed by a slightly written as “excluding the mother liquor”).

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, 18368-64-4, 2-Chloro-5-methylpyridine.

Reference:
Patent; CHANGSHU LEAGUE CHEMICAL CO LTD; CHEN, HUA; (6 pag.)CN103570612; (2016); B;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Adding a certain compound to certain chemical reactions, such as: 18368-64-4, 2-Chloro-5-methylpyridine, 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, 18368-64-4, blongs to pyridine-derivatives compound. Recommanded Product: 2-Chloro-5-methylpyridine

1.0 g (7.8 mmol) 2-chloro-5-methylpyridine are stirred under reflux in 5.7 ml (5.9 g, 117.6 mmol) hydrazine hydrate for 12 h. 10 ml ethylene glycol monoethyl ether are added to the cooled reaction mixture and the solvent is then removed completely on a rotary evaporator. This working step is repeated twice, methylene chloride is then added to the residue, the precipitate is filtered off, the filtrate is concentrated in vacuo and the residue is dried in vacuo.Yield: 644 mg (67% of th.)LC-MS (Method 8): Rt=0.35 min; MS (ESIpos): m/z=124 [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,18368-64-4, its application will become more common.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; US2010/305085; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.18368-64-4, name is 2-Chloro-5-methylpyridine, molecular formula is C6H6ClN, molecular weight is 127.57, as common compound, the synthetic route is as follows.Safety of 2-Chloro-5-methylpyridine

General procedure: 2-Trimethylsilylpyridine (1.2mmol), the aryl halide (1mmol), palladium acetate (0.10mmol), CataXCium A (0.2mmol), CuI (76mg, 0.4mmol) and KF (2.20mmol) were combined in reaction tubes in a Radleys green-house parallel synthesiser under a flow of nitrogen and degassed DMF (1ml) was added. The resulting suspensions were stirred at 90 oC under nitrogen for 12 hours. Reactions were analysed by LC-MS at 1mg/1ml in methanol to determine the yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Article; Blakemore, David C.; Marples, Louise A.; Tetrahedron Letters; vol. 52; 32; (2011); p. 4192 – 4195;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Electric Literature of 18368-64-4, 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. 18368-64-4, name is 2-Chloro-5-methylpyridine. A new synthetic method of this compound is introduced below.

2-Chloro-5-methyl-4-nitropyridine N-oxide () : Following the method of Z. Talik, A. Puszko, Roczniki Chemii Ann. Soc. Chim. Polonorum, 1976, 50, 2209, to a suspension of 2-chloro-5-methylpyridine (10 g, 0.078 mol) in acetic anhydride (25 mL), hydrogen peroxide 30% (25 mL) was added in small portions. This mixture was stirred at room temperature for 24 hours and then heated at 60 C for 30 hours. After removing the excess of acetic acid under reduced pressure, the residue was added in small portions to concentrated sulfuric acid (15 mL). The resulting solution was added to a mixture of concentrated sulfuric acid (15 mL) and fuming nitric acid (25 mL), and then heated at 100 C for 90 minutes. The reaction mixture was poured on ice, neutralized with solid ammonium carbonate and finally with aqueous ammonia until basic. A precipitate was then formed. After nitration, 10 was isolated as a pale yellow solid (9.4 g, 0. 050 mol, HPLC Rt 3.272 minutes, FIA ES+ 188.9, ES-188.0).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,18368-64-4, 2-Chloro-5-methylpyridine, and friends who are interested can also refer to it.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2003/91246; (2003); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem