Allyl chloride → N-allyl-2-methyl-4-nitroaniline

Participants

Reaction Conditions

Reaction Steps

60 g (0.33 mol) of N-formyl-2-methyl-4-nitroaniline were dissolved in 500 ml of dimethylformamide. 184 g (1.33 mol) of potassium carbonate were added, and the resultant solution was warmed to 50° C. 152.8 g (2 mol) of allyl chloride were added dropwise in the course of 50 minutes to the mixture at 50° C. When the alkylation reaction was complete, the resultant reaction mixture was warmed to 70° C. and 350 g of 1 N sodium hydroxide solution were slowly added dropwise. The resultant mixture was stirred at 70° C. for 2.5 hours and subsequently poured into 3 l of ice water. The precipitate was filtered off with suction, washed with water until neutral and subsequently dried at 50° C. under reduced pressure, to give 61 g of N-allyl-2-methyl-4-nitroaniline (yield: 95%), which was recrystallized as described under section 1.4 and then had the same physical chemical properties as the compound prepared in accordance with section 1.4.

Provenance & Evidence