Ammonia → Imiquimod

Participants

Reaction Steps

A mixture of 6.0 g (0.023 mole) of 4-chloro-1-isobuty-I-1H-imidazo[4,5-c]quinoline (from Example 77) and 30 ml of 20% ammonia in methanol was heated in a steel bomb for 18 hours at 150° C. The bomb was cooled, and the solid was separated by filtration, washed with methanol and recrystallized from N,N-dimethylformamide to provide 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine, m.p. 292°-294° C. Analysis: Calculated for C14H16N4 : % C, 70.0; H, 6.7; % N, 23.3; Found: % C, 69.9; % H, 6.7; % N, 23.6.

Provenance & Evidence