Hydroxylamine → N'-Hydroxybenzenecarboximidamide

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.

1. customThe solvent was evaporated under reduced pressure and water (10 cm3)
2. additionwas added to the residue
3. extractionThe mixture was extracted with dichloromethane (100 cm3)
4. extractionthe organic extract
5. customwas evaporated under reduced pressure
6. customThe residue was purified by column chromatography

ORD record

ord-f582b78e770941c3ad8bc5fcd23d5a34

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07838483B2