反应详情

To a solution of 0.76 g (4.39 mmol) of 8-hydroxyquinoline-5-carboxaldehyde (G. R. Clemo and R. Howe, J. Chem. Soc., 1955, 3552) in 5 mL of dimethyl sulfoxide was added 0.24 g (4.4 mmol) of sodium methoxide, while keeping the mixture under nitrogen. After stirring for 5 min, 0.56 g (4.4 mmol) of dimethyl sulfate was added. The reaction was stirred for 1 hr and the solvent removed under vacuum. The residue was partitioned between dichloromethane (100 mL) and 0.5N sodium hydroxide (50 mL); the organic layer was washed with water (100 mL), dried over anhydrous magnesium sulfate, and concentrated to give 0.61 g (74%) of 8-methoxyquinoline-5-carboxaldehyde, mp 121°-122° after recrystallization from ethanol-hexane (2:25). Anal. Calcd for C11H9NO2 : C, 70.58; H, 4.85; N, 7.48. Found: C, 70.55; H, 4.91; N, 7.44.

1. stirringThe reaction was stirred for 1 hr
2. customthe solvent removed under vacuum
3. customThe residue was partitioned between dichloromethane (100 mL) and 0.5N sodium hydroxide (50 mL)
4. washthe organic layer was washed with water (100 mL)
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated