Diethyl Ether → 4-(Methylamino)pyridine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

4-Chloronicotinonitrile (45.0 g, 324 mmol) was suspended in water (250 mL) and 41% aqueous methylamine solution (250 mL). The resultant mixture was heated, with stirring, at 90° C. for 1 hour before the mixture was cooled to room temperature and extracted with ethyl acetate (×2). The combined organic layers were washed with water, followed by brine then dried (MgSO4) and evaporated to provide a residue. Trituration of the residue with diethyl ether gave the title compound (40.4 g, 93%) as a white solid. 1H NMR (CDCl3) 2.98 (3H, d, J=5.1 Hz), 5.20 (1H, br s), 6.53 (1H, d, J=6.13 Hz), 8.35 (1H, d, J=6.13 Hz), 8.43 (1H, s).

Provenance & Evidence