Hydroxylamine → N'-Hydroxybenzenecarboximidamide

Participants

Reaction Steps

Benzonitrile (0.99 cm3, 1 g, 9.7 mmol) and hydroxylamine (50% in water, 0.89 cm3, 0.96 g, 14.55 mmol, 1.5 eq) were stirred under reflux in EtOH (10 cm3) for 48 hours. The solvent was evaporated under reduced pressure and water (10 cm3) was added to the residue. The mixture was extracted with dichloromethane (100 cm3) and the organic extract was evaporated under reduced pressure. The residue was purified by column chromatography to give the product N′-hydroxybenzimidamide (1.32 g, 100%) as a white crystalline solid, mp 79-81° C. (lit 79-80° C. This procedure is suitable for all starting materials bearing a benzene ring.

Provenance & Evidence