Hydrochloric Acid → N-Methyl-N-(3-nitrophenyl)acetamide

Participants

Reaction Steps

To a suspension of sodium hydride (60% in oil, 5.19 g) in N,N-dimethylformamide (30 ml) was added a solution of 3′-nitroacetanilide (214 mg) in N,N-dimethylformamide (30 ml) at 0° C. The mixture was stirred at room temperature for 30 minutes, then iodomethane (3.59 ml) was added. After 30 minutes, 1N hydrochloric acid was poured into the mixture and extracted with ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give N-methyl-3′-nitroacetanilide (4.64 g).

Provenance & Evidence