4-Cyanopyridine → Pyridine-4-amidine hydrochloride

Participants

Reaction Steps

A solution of 4-pyridinecarbonitrile (370 g, 3.55 mol) and sodium methoxide (20.0 g, 0.37 mol) in methanol (1.71) was stirred at room temperature for 1.5 hours, then ammonium chloride (200 g, 3.7 mol) was added. The reaction mixture was stirred for 24 hours, the resulting solid was collected by filtration and the filtrate was evaporated to dryness. The two crops were combined and recrystallized from water to afford 394 g (70%) of 4-pyridinecarboxamidine hydrochloride, m.p. 250°-252° C. (dec.).

Provenance & Evidence