Acetic Acid → N-(2-Hydroxy-4-nitrophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

Acetic anhydride (398 g, 3.90 mol) was added to a stirred suspension of 2-amino-5-nitro-phenol (400 g, 2.60 mol) and acetic acid (1.60 L) at 62.5° C. The reaction mixture was stirred at 62.5° C. for 1 hour, and then cooled to room temperature. Water (2.00 L) was added over 20 minutes to the stirred reaction mixture. After stirring for 1 hour, the solid was collected by vacuum filtration and washed with water and heptane. Drying the product in vacuo at 60° C. yielded 486.7 g (96%, 99.5% by HPLC) of N-(2-hydroxy-4-nitro-phenyl)-acetamide. 1H NMR (DMSO-d6) δ (ppm) 2.18 (s, 3H), 7.70 (m, 2H), 8.30 (d, 1H), 9.45 (s, 1H), 11.00 (s, 1H).

Provenance & Evidence