2-Chloro-4-(dimethylamino)nicotinonitrile

Synthesis

98694-71-4

147992-80-1

A slurry was prepared from 2-(1,3-bisdimethylamino-allyl)malononitrile (120.0 g, 632 mmol) in methanol (1500 mL). HCl gas was slowly passed at 0 °C and the reaction mixture became homogeneous after about 1 hour. Stirring was maintained at 0 °C and continued for 9 h under continuous passage of HCl gas. Subsequently, N2 was bubbled through the reaction mixture for 2 hours to remove residual HCl and then evaporated to remove all solvent. The residual solid was redissolved in CH2Cl2 and washed sequentially with water, aqueous K2C2O3 and water. The organic layer was separated and dried with Na2SO4. After filtration to remove the desiccant, the solvent was evaporated under reduced pressure to give the pure product 2-chloro-4-(dimethylamino)nicotinonitrile (113.0 g, 98% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.96 ppm (d, J=6.4 Hz, 1H); 6.59 (d, J=6.4 Hz, 1H); 3.30 (s, 6H). Mass spectrum (ESI, M+1): 181.9.

References