Citric Acid → 4-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol

Participants

Reaction Steps

Aqueous sodium hydroxide (700 mL of 2 N) was added to a stirred suspension of 3-(4-chloro-2-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)propyl 1H-imidazole-1-carboxylate (38 g, 0.010 mol) in methanol (100 mL), and the resulting solution was stirred for two hours at room temperature and then adjusted to pH 7 with the addition of 10% w/w aqueous citric acid. A precipitate formed, and the mixture was stirred overnight. The precipitate was isolated by filtration and washed with acetonitrile to provide 24 g of 4-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol.

Provenance & Evidence