Sodium Hydroxide → 1H-indole-2-carbonitrile

Participants

Reaction Steps

A solution of indole-2-carboxamide (3.02 g, 18.8 mmol) in dichlorophenylphosphine oxide (20 mL) was heated at 80° C. overnight. The cooled reaction mixture was then poured over 100 mL ice and the pH was adjusted to 11 with 50% aqueous sodium hydroxide. Extraction with ethyl acetate followed by concentration in vacuo gave an off-white solid which was purified by silica gel chromatography (1% MeOH/CH2Cl2) to yield the title compound (2.41 g, 90%): 1H NMR (400 MHz, DMSO-d6) δ 7.68 (d, 1H), 7.46 (d, 1H), 7.36 (s, 1H), 7.34 (t, 1H), 7.14 (t, 1H).

Provenance & Evidence