Sodium Hydroxide → HCID 9899727, compound

Participants

Reaction Steps

A solution of boron tribromide in dichloromethane (1M; 8.5 ml, 8.5 mmol) was added dropwise under nitrogen to an ice-cooled, stirred suspension of 3-(3-methoxybenzyl) isoquinolinone (1 g, 3.8 mmol) in dichloromethane (5 ml), the stirred mixture was heated under reflux for 6 hours, then it was cooled to ambient temperature and poured onto 10% aqueous sodium hydroxide solution (30 ml). The basic solution was washed with dichloromethane (3×50 ml), then it was acidified by the addition of concentrated hydrochloric acid. The product was extracted into ethyl acetate (3×50 ml), the combined extracts were dried (MgSO4) and the solvent was removed in vacuo to leave 3-(3-hydroxybenzyl)isoquinolinone (0.4 g, 42%) as a white solid; m.pt. 225-227° C.; δH 3.80 (2H, s), 6.35 (1H, s), 6.60-7.70 (7H, m), 8.10 (1H, d), 9.30 (1H, s), 11.20 (1H, br s); m/z (M+H)+. 252 (100% purity).

Provenance & Evidence