Pyridine-2-carbonitrile → Pyridine-2-carboximidamide hydrochloride

Participants

Reaction Steps

To a solution of 2-cyanopyridine (20.0 g, 0.19 mol) in methanol (300 ml) under argon was added sodium methoxide (0.5 g). The reaction mixture was stirred at room temperature for 24 hours, then ammonium chloride (10.7 g, 0.2 mol) was added. The mixture was stirred at room temperature for 3.5 hours and the solvent was removed in vacuo. The residue was diluted with isopropanol (20 ml) and ether (400 ml) and a solid was collected by filtration to afford 28.2 g (87%) of 2-pyridinecarboxamidine hydrochloride as a white solid, m.p. 141°-142° C. when dried at 40° C. in high vacuum.

Provenance & Evidence