Methyl iodide → HCID 54136909, compound

Participants

Reaction Steps

A solution of N-butylindole-5-acetamide (1.0 g) in dimethylformamide (15 ml) was added to a slurry of sodium hydride (0.11 g) in dimethylformamide (7 ml) at 0° under a nitrogen atmosphere, stirred for 1 hr at 0° and treated with iodomethane (0.3 ml). The reaction was quenched with saturated ammonium chloride solution and diluted with water. The precipitate that formed was collected by filtration, washed with water, and dried under vaccum to give N-butyl-1-methyl-indole-5-acetamide (0.46 g, 43%) as a pale yellow powder: NMR (250 MHz, CDCl3): 0.84(t, 3H, N(CH2)3CH3), 1.38-1.17(m, 4H, NCH2 (CH2)2), 3.16(q, 2H, NCH2), 3.67(s, 2H, ArCH2), 3.80(s, 3H, NCH3), 5.43(br, 1H, NH), 6.45(d, 1H, H2 -indole).

Provenance & Evidence