Hydroxylamine → Methyl 5-[amino(hydroxyimino)methyl]-2-chlorobenzoate

Participants

Reaction Steps

Methyl 2-chloro-5-cyanobenzoate (1.55 g; 7.92 mmol; 1 eq.) was suspended in EtOH (31 mL). Hydroxylamine (1.17 mL; 39.62 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 6 hours. The mixture was concentrated affording the title compound as a beige solid (1.65 g, 91%). 1H NMR (DMSO-d6, 300 MHz) δ 9.92 (br s, 1H), 8.19-8.18 (m, 1H), 7.92-7.90 (m, 1H), 7.68-7.65 (m, 1H), 6.04 (br s, 2H), 3.95 (s, 3H). LC/MS (Method B): 229.0 (M+H)+; 227.0 (M−H)−.

Provenance & Evidence