1,4-Dioxane → 3-Fluoro-7-(2-methoxyethoxy)quinoline-2-carbaldehyde
Reaction equation
[F:1][C:2]1[C:3]([CH3:17])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=2.[O:18]1CCOCC1>O>[F:1][C:2]1[C:3]([CH:17]=[O:18])=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:6]=2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-fluoro-7-(2-methoxyethoxy)-2-methylquinoline (0.234 g, 0.995 mmol) and SeO2 (0.132 g, 1.19 mmol) in dioxane (10 mL) and water (0.1 mL) was stirred at 102° C. (bath) for 5 hours. The solid was removed by filtration. The filtrated was concentrated under reduced pressure. The residue obtained was purified by flash chromatography (1:1 hexane/ethyl acetate) to give 3-fluoro-7-(2-methoxyethoxy)quinoline-2-carbaldehyde (0.24 g, 0.963 mmol, 97% yield) as a solid.