Hydrogen Peroxide → 2-Hydroxyquinoline

Participants

Reaction Steps

Aqueous hydrogen peroxide (27.5 wt % solution in water, 145 μl) was added to a solution of 3-formyl-2-heptyl-4(1H)-quinolone (1 mmol) in EtOH (3 ml) and 1M NaOH solution (1.0 ml) under nitrogen, and the mixture was stirred at room temperature for 6 hours. The precipitate was removed by filtration, air dried and crystallised from EtOAc to give 2-heptyl-3-hydroxy-4(1M-quinolone in 70% yield as off-white needles, mp 195-197° C.

Provenance & Evidence