Selenium Dioxide → 6-Fluoro-8-isopropoxyquinoline-2-carbaldehyde
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1)[N:8]=[C:7]([CH3:16])[CH:6]=[CH:5]2.[Se](=O)=[O:18]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH:13]([CH3:14])[CH3:15])[CH:11]=1)[N:8]=[C:7]([CH:16]=[O:18])[CH:6]=[CH:5]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 6-fluoro-8-isopropoxy-2-methylquinoline (1.1 g, 5.02 mmol) in dioxane/water (3.5 ml/0.3 mL) at ambient temperature was added selenium dioxide (0.668 g, 6.02 mmol) and the reaction was heated to reflux for 2-3 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 crude material was purified by reverse phase chromatography (SP4, 25M, eluting with a gradient of water/ACN 100:0 to 0:100, 20 column volumes) to yield 6-fluoro-8-isopropoxyquinoline-2-carbaldehyde (410 mg, 35.0% yield) as a tan solid.