Hydroxyamine hydrochloride → N'-Hydroxy-(5-bromo-1H-3-indolyl)ethanimidamide

Participants

Reaction Steps

To a solution of sodium methoxide (16.92 mL, 0.074 mol, 25 wt %/methanol) in methanol (120 mL) was added powdered hydroxylamine hydrochloride (5.66 g, 0.0814 mol). The mixture was heated at reflux for 1 hour. 5-Bromo-3-indolylacetonitrile (8.8 g, 0.37 mol) was added and refluxing was continued overnight. Refluxing was continued for a further 3 hours. The reaction was cooled to room temperature and concentrated under reduced pressure to obtain a pale yellow solid. The solid was suspended in water (100 mL), stirred for 1/2 hour, filtered, air dried and stirred in ether (40 mL) to give 7.91 g (71%) of product as a white solid.

Provenance & Evidence