Adding a certain compound to certain chemical reactions, such as: 92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, 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, Product Details of 92138-35-7, blongs to pyridine-derivatives compound. Product Details of 92138-35-7
100 L jacketed reactor equipped with a temperature probe, nitrogen inlet and reflux condenser was charged with toluene (27.0 L, 30 vol.) and EtOH (5.4 L, 6 vol.) followed by 6-chloro-3-nitropyridin-2(1H)-one (900.0 g, 5.15 mol) and phenyl boronic acid (640.4 g, 5.253 mol). The mixture was stirred at ambient temperature for 15 minutes before a solution of K2CO3 (173.9 g, 11.33 mol) in DI water (5.4 L, 6 vol.) was added. The reaction mixture was degassed with argon for 30 minutes at room temperature. Tetrakis triphenylphosphine palladium (178.2 g, 3 mol %) was added and the solution was heated to 95-100 C. (internal temperature was 77-79 C.) and stirred for 3 hours. After 3 hours HPLC showed 2.8% of starting material and another single impurity (15.3%, 1.17 RRT). The reaction was maintained for 3 hours at same temperature. After 6 hours, there was no progress in the reaction and the mixture was cooled to room temperature, degassed for 30 minutes, and another 5.0 g of tetrakis triphenylphosphine palladium was added and the solution was heated to 95-100 C. Reaction was deemed complete after one hour by HPLC. The reaction mixture was cooled to room temperature, the reaction was diluted with DI water (11.7 L, 13 vol.) followed by EtOAc (18.0 L, 20 vol.) and stirred for 1 hour. The two layers were separated, leaving the solids in aqueous layer. The aqueous layer was extracted with EtOAc (13.5 L, 15 vol.). The combined aqueous layers were neutralized pH to 6.2-6.8 with 3N HCl, when more solids precipitated out, the solids were filtered off, washed with water (2×2.5 L, 5 vol.) and dried under vacuum at 45-50 C. for 48 hours, to furnish 1a (761.1 g, 68.9% yield, 78.0% purity) as yellow solid. The compound was characterized by 1H NMR (DMSO-d6) and MS. (0157) The combined organic (ethyl acetate) layers were extracted with 3N NaOH (15 L), when solids were formed. The organic layer was separated. The aqueous layer was then acidified pH to 5-6 with 3N HCl, when more solids were precipitated out, which were filtered off and washed with DI water (2.0 L) and dried to obtain compound 1a (140.0 g, 12.7%, 93.8% purity, 2nd crop).
At the same time, in my other blogs, there are other synthetic methods of this type of compound,92138-35-7, 6-Chloro-3-nitropyridin-2(1H)-one, and friends who are interested can also refer to it.
Reference:
Patent; ArQule, Inc.; Bates, Craig; Chen, Jian-Xie; Mao, Jianmin; Reed, David P.; US2015/266876; (2015); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem