2-(pyridin-4-ylmethylamino)nicotinic acid

3731-53-1

2942-59-8

854382-06-2

General procedure for the synthesis of 2-[(4-pyridinylmethyl)amino]nicotinic acid from 4-methylaminopyridine and 2-chloronicotinic acid: 2-chloronicotinic acid (25.3 mmol), a catalytic amount of copper oxide, and potassium carbonate (25.3 mmol) were added to a 100 mL round-bottomed flask, which was stirred at room temperature for 20 minutes. Subsequently, 4-dimethylaminopyridine (50.6 mmol) was added and the reaction mixture was heated to 110°C and maintained for 2 hours. After completion of the reaction, ethyl acetate was added, stirred to room temperature and then filtered. The filter cake was first washed twice with ethyl acetate and then dissolved in 20 mL of water. The pH of the solution was adjusted to 5-6 with 4N hydrochloric acid, left to stand and then filtered. The resulting filter cake was dried to obtain the crude product. The product was further purified by hot pulping with ethanol, and 5.16 g of off-white solid was obtained after filtration in 89% yield.