Water → N-t-butoxycarbonyl-N-methyl-5-methoxy-2-nitroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution at 0° C. of N-(5-methoxy-2-nitrophenyl)carbamic acid t-butyl ester (5.5 g) in dimethylformamide (35 ml) was added sodium hydride (0.9 g, 60% dispersion in mineral oil) and the mixture was stirred at 0° C. for 1 hour. A solution of dimethyl sulfate (2.2 ml) in dimethylformamide (5.5 ml) was slowly added dropwise at 0° C. and the mixture was stirred at the same temperature for 0.5 hours. At the end of this time, to the reaction mixture was slowly added water (55 ml) and the mixture was extracted with toluene (66 ml). The extract was washed with water and concentrated in vacuo to give the desired compound (5.8 g, yield 100%).

Provenance & Evidence