Nitric Acid → N-(5-Bromo-4-methoxy-2-nitrophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To a cold (5° C.) solution of 3.36 g (13.8 mmol) of 2-Bromo-4-acetaminoanisole in 5 mL of acetic anhydride and 10 mL of acetic acid, was added dropwise 0.9 mL (13.8 mmol) of concentrate nitric acid. The resulting solution was stirred at 5° C. for 3 h, poured into 90 mL of water, stirred, and filtered to collect the solid (the desired product). The solid was washed twice with cold water, dried under vacuo at 100° C., crystallized from chloroform to give 3.26 g (82% yield) of pure compound 6. 1H NMR (CDCl3) δ 10.2 (s, 1 H, NH), 9.09 (s, 1 H), 7.67 (s, 1 H), 3.95 (s, 3 H, OMe), 2.28 (s, 3 H, CH3).

Provenance & Evidence