O-Methylhydroxylamine hydrochloride → HCID 72448476, compound

Participants

Reaction Steps

Methoxylamine hydrochloride (22.8 g, 272 mmol) was added to a solution of 1-(4,4-dimethoxybutyl)-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine (36.6 g, 136 mmol) in ethanol (200 mL). The reaction mixture was stirred at room temperature for two hours, then was concentrated under reduced pressure. The residue was diluted with water and brought to pH 7 with saturated aqueous sodium bicarbonate. The mixture was extracted with 5% methanol/dichloromethane. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, elution with 5% methanol in dichloromethane) followed by recrystallization from ethyl acetate to yield 4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal O-methyloxime as an off-white powder, mp 153-155° C.

Provenance & Evidence