Selenium Dioxide → 7-Isopropoxy-8-methylquinoline-2-carbaldehyde

Participants

Reaction Steps

To 7-isopropoxy-2,8-dimethylquinoline (120 mg, 0.557 mmol) in dioxane/water (5 mL/0.5 mL) at ambient temperature was added selenium dioxide (74.2 mg, 0.669 mmol) and the reaction was heated to reflux for 2 hours. After cooling, the reaction was filtered and the solids were washed with DCM. The filtrate was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography (SP4, 12M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 7-isopropoxy-8-methylquinoline-2-carbaldehyde (45 mg, 35.2% yield) as a tan solid.

Provenance & Evidence