6-Methoxyquinoline → 6-Hydroxyquinoline

Participants

Reaction Steps

A solution of 2.50 g (15.7 mmol, Aldrich) of 6-methoxyquinoline in 10 ml of 48% aqueous HBr was refluxed for 24 hours. The reaction mixture was cooled, added slowly to a 150 ml stirred solution of saturated aqueous sodium bicarbonate and then extracted with two 100 ml portions of ethyl acetate. The organic extracts were combined, dried (MgSO4) and concentrated in vacuo to give a solid. The crude material was recrystallized (EtOAc/petroleum ether) to afford 1.95 g (84%) of title compound as white crystals, m.p. 194°-195°.

Provenance & Evidence