Water → 2-(1-methyl-1H-indol-7-yl)acetamide

Participants

Reaction Steps

A slurry of (1-methyl-1H-indol-7-yl)-acetonitrile (137 mmol, crude material prepared as described above) in tert-butanol (240 mL) was heated to reflux, KOH (85%, 88.3 g, 1.57 mol) was added and mixture was stirred at reflux for 15 minutes. H2O (1 mL) was introduced and the mixture was heated at reflux for an additional 5 minutes. The solution was allowed to cool, decanted, and diluted with EtOAc (1 L) and H2O. The two layers were separated and the organic solution was washed with H2O and brine. The crude solution was dried (MgSO4), filtered and concentrated to an off-white solid. Trituration with refluxing ether gave the title compound (16.90 g, 65% from 1H-indole-7-carboxaldehyde). 1H NMR (400 MHz, DMSO-d6) 3.87 (s, 2H), 4.03 (s, 3H), 6.39 (d, J=3.2 Hz, 1H), 6.83–7.01 (m, 3H), 7.20 (d, J=3.3 Hz, 1H), 7.30–7.46 (m, 2H). MS (electrospray, m/z) 189.0 (M++1). Anal. Calcd for C11H12N2O: C, 70.19; H, 6.43; N, 14.88. Found: C, 70.03; H, 6.41; N, 14.63.

Provenance & Evidence