O-ethylhydroxylamine hydrochloride → 1-phenoxy-2-propyl-1H-imidazo[4,5-c]quinoline

Participants

Reaction Steps

The method of Part B of Example 20 was followed using N-(4-chloroquinolin-3-yl)butyramide (3.5 g, 14 mmol) in lieu of 4-chloroquinolin-3-ylformamide and O-phenylhydroxylamine hydrochloride (2.3 g, 16 mmol) in lieu of O-ethylhydroxylamine hydrochloride in isopropanol (100 mL). Chromatographic purification was carried out eluting with 5% methanol in dichloromethane containing 2 mL of aqueous ammonium hydroxide per liter of eluent to provide 1.58 g of 1-phenoxy-2-propyl-1H-imidazo[4,5-c]quinoline as a brown, foamy solid.

Provenance & Evidence