Benzyloxyamine hydrochloride → 1-benzyloxy-2-propyl-1H-imidazo[4,5-c]quinoline

Participants

Reaction Steps

A solution of N-(4-chloroquinolin-3-yl)butyramide (20.0 g, 80.4 mmol) and O-benzylhydroxylamine hydrochloride (16.0 g, 0.100 mol) in ethanol (150 mL) was heated at reflux overnight and allowed to cool to room temperature. A precipitate was present, and the mixture was cooled to approximately 0° C. The precipitate was collected by filtration and purified by column chromatography on silica gel (eluting with 5% methanol in dichloromethane containing 3 mL of aqueous ammonium hydroxide per liter of eluent) to provide 1-(benzyloxy)-2-propyl-1H-imidazo[4,5-c]quinoline and 2-propyl-1H-imidazo[4,5-c]quinolin-1-ol.

Provenance & Evidence