Ammonium Acetate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[5-chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone (76 mg, 0.25 mmol) and ammonium acetate (195 mg, 2.54 mmol) in methanol (1.4 mL) and acetonitrile (1.4 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling, sodium cyanoborohydride (31.9 mg, 0.507 mmol) was added to the resultant mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature, quenched with saturated sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and then evaporated to dryness. The residue was used directly in next step (52 mg, 68%). LCMS calculated for C17H15ClFN2(M+H)+: m/z=301.1; found: 301.0.

Provenance & Evidence