反应详情

To a solution of 2-methylquinoline-8-carbonitrile (1.70 g, 10.1 mmol) in 1,4-dioxane (50 mL) and water (1 mL), was added selenium dioxide (2.80 g, 25.3 mmol) and the resulting mixture heated at reflux for 7 hours. After cooling to ambient temperature, the solids formed were removed by filtration through a pad of Celite® and washed with 1:1 mixture of ethyl acetate/dichloromethane (50 mL). The filtrate was concentrated under reduced pressure and the residue obtained purified by column chromatography (Biotage, 40M; 1% MeOH: dichloromethane) to give 2-formylquinoline-8-carbonitrile (1.51 g, 82%).

1. temperaturethe resulting mixture heated
2. temperatureat reflux for 7 hours
3. customthe solids formed
4. customwere removed by filtration through a pad of Celite®
5. washwashed with 1:1 mixture of ethyl acetate/dichloromethane (50 mL)
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue obtained
8. custompurified by column chromatography (Biotage, 40M; 1% MeOH: dichloromethane)