Sodium cyanoborohydride → HCID 86612266, compound

Participants

Reaction Steps

Sodium cyanoborohydride (16.0 g, 254 mmol) was added to a solution of 4-(4-amino-2-methyl-1H-imidazo[4,5-c]quinolin-1-yl)butanal O-methyloxime (prepared as described in Example 45, 15.1 g, 50.8 mmol) in ethanol (100 mL) and acetic acid (15 mL). The reaction mixture was stirred at room temperature for 2 hours, additional acetic acid (15 mL) was added, and stirring was continued for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and adjusted to pH 7 with saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane. The organic layers were combined, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated to provide 12.1 g of 1-[4-(methoxyamino)butyl]-2-methyl-1H-imidazo[4,5-c]quinolin-4-amine.

Provenance & Evidence