Hydroxylamine → N-Hydroxy-4-(hydroxymethyl)benzimidamide

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(hydroxymethyl)benzonitrile (11.05 g; 83.08 mmol) in EtOH (100 mL) was added hydroxylamine (27.4 mL; 415 mmol) (50% in water) and the mixture was heated to 74° C. for 16 hours. The mixture was poured into a crystallizing dish and the solvent were evaporated. The residue was washed with copious amounts of EtOAc, dry MeOH and dry MeCN which was filtered through a hydrophobic frit and the solvent removed in vacuo to give the title compound as a white solid (13.1 g, 95%). 1H NMR (DMSO-d6, 400 MHz) δ 9.58 (s, 1H), 7.70-7.62 (m, 2H), 7.34 (d, J=8.1 Hz, 2H), 5.79 (s, 2H), 5.23 (t, J=5.6 Hz, 1H), 4.54 (d, J=5.6 Hz, 2H).

Provenance & Evidence