Dimethylformamide → N,1-dimethylindole-2-carboxamide

Participants

Reaction Steps

To a stirred solution of ethyl indole-2-carboxylate (25.0 g, 132.1 mmole) in dry DMF (100 mL) at 5° C. was added 60% NaH (6.9 g, 171.7 mmole). After 10 min, methyl iodide (56.2 g, 396.3 mmole) was added and the reaction slurry was allowed to warm RT and stirred for 12 hr. The reaction contents were poured into H2O (200 mL) and extracted with EtOAc (2×150 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure gave a yellow oil. This oil was suspended in a 40% methylamine/H2O solution (100 mL) containing THF (50 mL) and stirred vigorously at RT for 24 hr. The reaction solution was concentrated under vacuum to remove the THF and then poured into H2O (400 mL). The precipitate was filtered, washed with H2O and dried under vacuum at RT to afford the title compound (23.3 g, 94%) as a white solid: MS (ES) m/e 189 (M+H)+.

Provenance & Evidence