Nitric Acid → N-(5-Fluoro-2-nitrophenyl)acetamide

Participants

Reaction Steps

N-methylcarbonyl 3-fluoroaniline (5 g, 32.0 mmol) is dissolved in 25 ml of conc. sulfuric acid and is cooled to 0°. A mixture of 90% nitric acid (2.5 ml) in conc. sulfuric acid (25 ml) is added dropwise over a period of about 1 hour, with the temperature maintained at 0°. The reaction is allowed to warm to RT and is stirred at RT for 3 hours. The reaction is then carefully poured into ice. The resulting solid is washed several times with 10% ethyl acetate/hexane, and the combined organic extracts are stripped to give N-methylcarbonyl 2-nitro-5-fluoroaniline.

Provenance & Evidence