Pyridine → Phenyl pyridin-3-ylcarbamate

Participants

Reaction Steps

To a solution consisting of pyridin-3-yl amine (9.49 g, 101 mmol) and pyridine (8.77 g, 111 mmol) in CH3CN (80 mL) at 0° C. was added phenyl chloroformate (15.8 g, 101 mmol) dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 2 h. The reaction was quenched with H2O (200 mL) and the resulting precipitate was filtered and dried under vacuum to provide the title compound as a tan solid (17.34 g, 80%). MS (ESI+): calcd for C12H10N2O2 m/z 214.07, found 215.3 (M+H)+. 1H NMR (500 MHz, d6-DMSO): 10.46 (s, 1H), 8.69 (d, J=2.4 Hz, 1H), 8.27 (dd, J=4.7, 1.4 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.47-7.41 (m, 2H), 7.37 (dd, J=8.4, 4.7 Hz, 1H), 7.31-7.22 (m, 3H).

Provenance & Evidence