1,4-Dioxane → 7-(2-Hydroxyethyl)quinoline-2-carbaldehyde
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH2:12][CH2:13][OH:14])=[CH:7][CH:8]=2)[N:3]=1.[O:15]1CCOCC1>O>[OH:14][CH2:13][CH2:12][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[CH:11][C:2]([CH:1]=[O:15])=[N:3]2)=[CH:8][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(2-methylquinolin-7-yl)ethanol (0.220 g, 1.17 mmol) was dissolved in dioxane (5 mL) and water (0.05 mL). The reaction was treated with SeO2 (0.156 g, 1.41 mmol) and the mixture was heated to reflux for 2 hours. After cooling to ambient temperature, the solid was removed by filtration and washed with DCM. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (ethyl acetate/hexanes 5:1) to give 7-(2-hydroxyethyl)quinoline-2-carbaldehyde (0.21 g, 1.04 mmol, 89% yield) as a solid.