6-Methoxyquinoline → 2-Hydroxy-6-methoxyquinoline

Participants

Reaction Steps

To a solution of 6-methoxyquinoline (2.08 g) in CHCl3 (45 mL) at r.t. was added m-chloroperoxybenzoic acid (3.38 g) portionwise over 10 min. After 30 min., CHCl3 (50 mL) was added and the solution washed with saturated aq. NaHCO3 (3×), dried (MgSO4) and concentrated. A portion of this material (500 mg) in DMF (10 mL) was treated with trifluoroacetic anhydride (TFAA) and stirred at r.t. for 17 hr. The TFAA was removed under vacuum and to the resulting solution was added water (60 mL). The mixture was extracted with EtOAc (6×) and the combined organics were dried (MgSO4) and concentrated. Trituration of the resulting material with acetone provided the title compound as a pale yellow solid.

Provenance & Evidence