Hydroxylamine → Methyl 4-[amino(hydroxyimino)methyl]-3-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 4-cyano-3-methoxybenzoate, obtained in step 1 (135 mg; 0.71 mmol; 1 eq.) in EtOH (1.35 mL) was added hydroxylamine (50% in water) (0.21 mL; 3.53 mmol; 5 eq.). The reaction mixture was stirred at 60° C. for 3 h. Solvent were removed to dryness, to afford the title compound as a white powder (191 mg; quantitative). 1H NMR (DMSO-d6, 300 MHz) δ 9.58 (br s, 1H), 7.56-7.51 (m, 3H), 5.71 (br s, 2H), 3.87-3.85 (m, 6H). HPLC (Method A), Rt 1.17 min (purity: 95.0%).

Provenance & Evidence