5-Hydroxyisoindoline-1,3-dione → 5-Hydroxy-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Steps

To a solution of 5-hydroxyphthalimide (19.8 g, 121 mmol) in AcOH (500 mL) was slowly added zinc dust (47.6 g, 729 mmol) in portions, then the mixture was heated at the reflux temp. for 40 min., filtered hot, and concentrated under reduced pressure. The reaction was repeated on the same scale and the combined oily residue was purified by column chromatography (1.1 Kg SiO2; gradient from 60% EtOAc/40% hexane to 25% MeOH/75% EtOAc) to give 5-hydroxyisoindolin-1-one (3.77 g): TLC (100% EtOAc) Rf0.17; HPLC ES-MS m/z 150 ((M+H)+).

Provenance & Evidence