Benzaldehyde → 3-(Hydroxyphenylmethyl)indole-5-carbonitrile

Participants

Reaction Steps

A solution of 5-cyanoindole (2.84 g, 20 mmol) and benzaldehyde (4.24 g, 40 mmol) in MeOH (100 mL) was treated with powdered NaOH (0.8 g, 20 mmol) and stirred at rt for 4 days. The solvent was partially removed in vacuo and the residue diluted with CH2Cl2, washed with water (3×), and dried over Na2SO4, filtered and evaporated to a solid which was triturated with hexanes to provide 3-(hydroxyphenylmethyl)indole-5-carbonitrile as a light yellow solid (4.9 g, 98%).

Provenance & Evidence