Cyclopropylamine → 4-Chloro-N-cyclopropylpyridine-2-carboxamide

Participants

Reaction Steps

A 0° C. solution of cyclopropylamine (0.645 g, 11.30 mmol) and DIEA (1.973 mL, 11.30 mmol) in THF (15 mL) was treated with 4-chloropicolinoyl chloride hydrochloride (0.8 g, 3.77 mmol) in one portion, stirred at RT for 2 h, diluted with EtOAc and washed with satd. NaHCO3, then brine. The organic layer was dried over Na2SO4 and concentrated to dryness to afford 4-chloro-N-cyclopropylpicolinamide (0.86 g, 116%). 1H NMR (400 MHz, DMSO-d6): δ 8.83 (d, J=5.0 Hz, 1H), 8.58 (d, J=5.3 Hz, 1H), 7.99 (d, J=2.1 Hz, 1H), 7.74 (dd, J=5.3, 2.2 Hz, 1H), 2.89-2.88 (m, 1H), 0.68-0.66 (m, 4H); MS (ESI) m/z: 197.1 (M+H+).

Provenance & Evidence