Nitric Acid → 4-Isopropyl-2-nitroaniline

Participants

Reaction Steps

20.0 G. (0.148 moles) of 4-isopropylaniline is added with stirring to 75 ml. of acetic anhydride at from 20° to 45° C. The reaction mixture is stirred at 35° C. for 1 hour. 11 Ml. of fuming nitric acid (specific gravity 1.5) is added at a temperature of from 25° to 35° C. over a period of 20 minutes and stirred for 3 hours. The acid mixture is added to a mixture of 180 ml. of water, 45 ml. of concentrated sulfuric acid and 142 ml. of ethanol with stirring. The reaction mixture is stirred overnight at room temperature, refluxed for 2 hours, neutralized with saturated sodium carbonate solution and extracted with chloroform. The chloroform layer is dried and evaporated in vacuo affording 35 g. of a dark orange oil which is used as is in the next step.

Provenance & Evidence