Acetic Acid → HCID 86052872, compound

Participants

Reaction Conditions

Reaction Steps

Sodium cyanoborohydride (0.22 g, 3.5 mmol) and acetic acid (2 mL) were added to 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyraldehyde O-methyloxime in ethanol (6 mL) and stirred for 2 hours. The pH of the reaction mixture was made basic with potassium carbonate and the reaction mixture was diluted with water (5 mL) and dichloromethane (50 mL). The layers were separated, and the organic layer was dried over potassium carbonate, filtered, and concentrated under reduced pressure to afford 0.62 g of crude material with a small amount of ethanol present. Silica gel (1 g) was added to the crude material and the mixture was heated for 2.5 hours at 100° C. The mixture was cooled and the material was filtered with a 1:1 mixture of dichloromethane and methanol. The filtrate was concentrated under reduced pressure to afford 0.35 g of O-methyl-N-[4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]hydroxylamine as an oil.

Provenance & Evidence