Ammonium Hydroxide → 3-(1-(Trifluoromethyl)cyclopropyl)propanamide

Participants

Reaction Steps

A solution of 3-(1-(trifluoromethyl)cyclopropyl)propanoic acid (0.2 g, 1.098 mmol) and oxalyl chloride (0.144 mL, 1.647 mmol) in DCM (5 mL) and DMF (1 drop) was stirred at RT for 2 h, then concentrated to dryness. The residue was co-evaporated with DCM (1×), then dissolved in THF (5 mL), added drop-wise to a solution of NH4OH (˜15 M, 1.07 mL, ˜16 mmol) in THF (5 mL) and stirred at RT for 0.5 h. The mixture was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4 and concentrated to dryness to afford 3-(1-(trifluoromethyl)cyclopropyl)propanamide (179 mg, 90%). 1H NMR (400 MHz, DMSO-d6): δ 7.30 (s, 1H), 6.77 (s, 1H), 2.16 (m, 2H), 1.75 (m, 2H), 0.85 (m, 2H), 0.71 (m, 2H).

Provenance & Evidence