Dimethylformamide → 4-chloro-alpha,alpha-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol

Participants

Reaction Steps

To a stirred solution of 1.5 g of crude 1-(2-acetoxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-5-oxide from Part C in 10 ml of dichloromethane and 2 ml of N,N-dimethylformamide was added 0.843 g (0.0055 mole) of phosphorus oxychloride. After stirring for one hour, the mixture was evaporated to dryness. Hydrochloric acid was added to the residue, then the mixture was basified with ammonium hydroxide. The product was separated by filtration, washed with water and dried. Recrystallization from ethanol of a portion of the product provided 4-chloro-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline, m.p. 196°-199° C. Analysis: Calculated for C14H14ClN3O: %C, 61.0; %H, 5.2; %N, 15.2; Found: %C, 60.9; %H, 5.3; %N, 15.1.

Provenance & Evidence