Acetic Acid → HCID 86612249, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanoborohydride (5.40 g, 86 mmol) was added to a mixture of 4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime (5.60 g, 17.2 mmol), acetic acid (30 mL), and ethanol (75 mL) and stirred for 1 hour. The reaction mixture was cooled to 0° C. and the pH was adjusted to 8 with 25% sodium hydroxide solution. The reaction mixture was then concentrated under reduced pressure and diluted with dichloromethane (200 mL) and saturated aqueous sodium bicarbonate solution (75 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (2×75 mL). The combined organics were washed with water (2×50 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 5.2 g of N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]-O-methyl-hydroxylamine as a light brown solid.

Provenance & Evidence