ethyl 4,6-dichloro-1-methyl-1H-indole-2-carboxylate → N,1-dimethylindole-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A suspension of ethyl 4,6-dichloro-1-methyl-1H-indole-2-carboxylate (1.06 g, 3.90 mmole) in 2.0 M CH3NH2/CH3OH (40 mL) in a sealed pressure bottle was heated in an oil bath preset at 50° C. A homogeneous solution formed within 2.5 hr. The reaction was kept at 50° C. for 17.5 hr, during which time a solid precipitated. The mixture was cooled to RT and poured into H2O (40 mL). The resulting mixture was concentrated on the rotavap to remove the methanol, and the solid was collected by suction filtration. This was washed with plenty of H2O and dried in high vacuum at 45-50° C. to afford the title compound (0.99 g, 99%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 7.29 (s, 1 H), 7.16 (d, J=1.5 Hz, 1 H), 6.86 (s, 1 H), 6.21 (br s, 1 H), 4.02 (s, 3 H), 3.02 (d, J=4.9 Hz, 3 H); MS (ES) m/e 257 and 259 (M+H)+.

Provenance & Evidence