2-Cyano-4-methylpyridine

1003-67-4

7677-24-9

1620-76-4

4-Methylpyridine-N-oxide (2.0 g, 18.3 mmol) was used as starting material and dissolved in nitroethane (25 mL). Subsequently, trimethylcyanosilane (2.0 g, 20.2 mmol) and N,N-dimethylcarbamoyl chloride (1.7 mL, 18.5 mmol) were added sequentially to this solution. The reaction mixture was stirred at room temperature for 5 days. Upon completion of the reaction, the mixture was concentrated under reduced pressure, combined with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phases were combined and the solvent was removed by evaporation under reduced pressure. The resulting crystals were collected by filtration, washed with diisopropyl ether and dried to afford the target product 2-cyano-4-methylpyridine (0.91 g, 42% yield). The product was characterized by 1H-NMR (CDCl3), δ: 2.43 (3H, s), 7.33 (1H, d, J = 5.1 Hz), 7.53 (1H, s), 8.57 (1H, d, J = 4.8 Hz).