O-Methylhydroxylamine hydrochloride → HCID 58869106, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (0.98 g, 11.79 mmol) was added to a solution of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one (3.8 g, 9.83 mmol) in ethanol (50 mL) and water (10 mL) and stirred at ambient temperature for 3 hours. The mixture was then concentrated under reduced pressure, diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (eluting with 5% methanol in dichloromethane) and recrystallized from methanol and water to afford 3.6 g of 5-(4-amino-7-phenyl-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentan-2-one O-methyloxime as a tan solid, mp 191-192° C. MS (APCI) m/z 416.2 (M+H+); C25H29N5O

Provenance & Evidence