Hydroxylamine → 4-[Amino(hydroxyimino)methyl]benzamide

Participants

Reaction Steps

A solution of 7 g hydroxylamine hydrochloride (0.10 mol) was dissolved in 15 ml of ethanol and cooled to 0°-5° C. To the mixture was added 2.3 g sodium (0.10 mol) dissolved in 30 ml ethanol. After generating the free hydroxylamine, 3.05 g of terephthalonitrile (23.8 mmol) suspended in 40 ml of ethanol was added dropwise to the ethanol solution. The mixture was then refluxed for 20 hours. The volume of solution was reduced to 5 ml, and upon cooling a precipitate formed which was filtered. The yield was 2.21 g (48%), m.p. 224-225° C (decomp.). The infrared spectrum (KBr pellet) showed formation of peaks at 2.91 μ and 2.98 μ (NH2), 306 μ (OH), and 6.07 and 6.26 μ (C=N).

Provenance & Evidence