Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-2-chloro-5-fluorobenzoate

Participants

Reaction Steps

Methyl 2-chloro-4-cyano-5-fluorobenzoate (1.65 g; 7.72 mmol; 1 eq.) was suspended in EtOH (33 mL). Hydroxylamine (1.14 mL; 38.62 mmol; 5 eq.) was added in one portion. The reaction mixture was stirred at RT for 6 hours. The obtained suspension was filtered affording the title compound as a beige solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.98 (br s, 1H), 7.74-7.67 (m, 2H), 6 (hr s, 2H), 3.87 (s, 3H). LC/MS (Method B): 247.0 (M+H)+; 245.1 (M−H)−. HPLC (Method A) Rt 1.80 min (Purity: 90.4%).

Provenance & Evidence