Extracurricular laboratory: Synthetic route of 6-Chloro-2-methylpyridin-3-amine

At the same time, in my other blogs, there are other synthetic methods of this type of compound,164666-68-6, 6-Chloro-2-methylpyridin-3-amine, and friends who are interested can also refer to it.

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.164666-68-6, name is 6-Chloro-2-methylpyridin-3-amine, molecular formula is C6H7ClN2, molecular weight is 142.59, as common compound, the synthetic route is as follows.Application In Synthesis of 6-Chloro-2-methylpyridin-3-amine

To an ice cold solution of 6-chloro-2-methylpyridin-3-amine (12 g, 84 mmol) and AcOH (5.1 g, 84 mmol) in MeOH (198 g, 250 mL) was dropwise added bromine (13.5 g, 84 mmol). The resulting solution was stirred at ice bath temperature overnight after which it was concentrated under vacuo. The obtained residue was dissolved in EtOAc and sequentially washed with saturated aqueous NaHCO3 solution, 10% Na2S2O3 aqueous solution, brine and dried (Na2SO4). The solvent was removed under vacuo and the obtained crude material was purified by flash chromatography to afford 4-bromo-6-chloro-2-methylpyridin-3-amine (12.6 g). 1H NMR (500 MHz, Chloroform-d) delta 7.30 (s, 1H), 4.04 (brs, 2H), 2.46 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,164666-68-6, 6-Chloro-2-methylpyridin-3-amine, and friends who are interested can also refer to it.

Reference:
Patent; H. Lundbeck A/S; Juhl, Karsten; Jessing, Mikkel; Langgard, Morten; Vital, Paulo Jorge Vieira; Kehler, Jan; Rasmussen, Lars Kyhn; Clementson, Carl Martin Sebastian; Marigo, Mauro; US2019/185489; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem