Ammonium Acetate → 1-[7-(1-Aminoethyl)-5-chloroquinolin-8-yl]pyrrolidine-3-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(7-acetyl-5-chloroquinolin-8-yl)pyrrolidine-3-carbonitrile (0.016 g, 0.053 mmol) and ammonium acetate (0.0411 g, 0.534 mmol) in methanol (1.0 mL) and acetonitrile (1.0 mL) was heated at 65° C. in a sealed tube for 1 hour. After cooling to room temperature, sodium cyanoborohydride (0.010 g, 0.16 mmol) was added. The reaction was heated at 65° C. overnight. The mixture was cooled to room temperature, quenched with sat. NaHCO3 solution and extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to give the desired product. LCMS calculated for C16H18ClN4 (M+H)+: m/z=301.1; Found: 301.1.

Provenance & Evidence