8-Hydroxyquinoline → 8-Hydroxyquinoline N-oxide

Participants

Reaction Steps

To a solution of 8-hydroxyquinoline (1.45 g, 10 mmol) in dichloromethane (50 ml) was added 3-chloroperbenzoic acid (MCPBA) (1.24 g, 13 mmol). The mixture was stirred at room temperature for 10 min, poured into 1.0N sodium bicarbonate (100 ml), and then extracted with dichloromethane (3×50 ml). The extract was washed with water, dried over magnesium sulfate, and evaporated to give a brown solid which was crystallized from dichloromethane and diethyl ether affording 8-Hydroxyquinoline 1-oxide (5a) (1.34 g, 83%) as yellow needle crystals. mp: 132°-133° C.; 1H-NMR (CDCl3): δ7.04-8.28 (m, 6H, Ar--H), 15.02 (br s, 1H, OH).

Provenance & Evidence