Benzonitrile → N'-Hydroxybenzenecarboximidamide

Participants

Reaction Steps

To a stirred solution of sodium (0.48 g, 210 mmol) in methanol (210 ml) was added a solution of hydroxylamine hydrochloride (15.4 g, 221 mmol) in methanol (70 ml). The mixture was stirred at room temperature for 10 minutes before addition of benzonitrile (20.4 ml, 200 mmol) and the reaction stirred at room temperature overnight. The mixture was filtered through a pad of Celite and the flitrate concentrated in vacuo to approximately 100 ml. Diethyl ether (200 ml) was added and the precipitate filtered. The filtrate was evaporated in vacuo to dryness, and on drying the title compound was obtained as a waxy white solid (27.1 g, 100%). δH (DMSO-d6) 5.92 (2H, br s, NH2), 7.35-7.41 (3H, m, ArH), 7.65-7.91 (2H, m, ArH), 9.69 (1H, br s, OH).

Provenance & Evidence