Ammonium Acetate → 1-(2-(4-aminocyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one

Participants

Reaction Steps

To 1.5 mL of an ethanol solution containing 10 mg of 7-methoxy-4-methyl-1-(2-(4-oxocyclohexyl)ethyl)quinolin-2(1H)-one, 3.7 mg of ammonium acetate and 15 mg of molecular sieves 3A were added at room temperature, the mixture was stirred for 1 hour, then thereto was added 5.0 mg of sodium cyanoborohydride, and the mixture was stirred at the same temperature for 4 hours and 30 minutes. Thereto was further added 3.0 mg of sodium cyanoborohydride, and the mixture was stirred for 30 minute, and then left to stand overnight. The solvent was removed under reduced pressure, water and ethyl acetate were added thereto, the reaction mixture was adjusted to pH 3 to 4 (pH test paper) with 2.0 mol/L hydrochloric acid, and the aqueous layer was separated. The aqueous layer was added with ethyl acetate, and the resultant solution was adjusted to pH 8 to 9 (pH test paper) with a 2.0 mol/L aqueous sodium hydroxide solution. The organic layer was separated, washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain 6.0 mg of a colorless oily substance, 1-(2-(4-aminocyclohexyl)ethyl)-7-methoxy-4-methylquinolin-2(1H)-one.

Provenance & Evidence