反应详情

To a solution of 2-methylquinolin-8-yl trifluoromethanesulfonate (3.0 g, 10.3 mmol) in acetonitrile (26 mL) was added sodium cyanide (1.0 g, 20.6 mmol). The solution was degassed under nitrogen for 10 minutes, followed by addition of copper (I) iodide (0.20 g, 1.03 mmol) and Pd(PPh3)4 (0.60 g, 0.52 mmol) under nitrogen. The mixture was heated at reflux for 2 hours. After cooling the mixture was diluted with ethyl acetate (50 mL) and filtered through Celite and washed with ethyl acetate (50 mL). The filtrate was washed with water and brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage, 40 M; 20% ethyl acetate:hexanes) to afford 2-methylquinoline-8-carbonitrile (1.70 g, 98%).

1. customThe solution was degassed under nitrogen for 10 minutes
2. temperatureThe mixture was heated
3. temperatureat reflux for 2 hours
4. temperatureAfter cooling the mixture
5. filtrationfiltered through Celite
6. washwashed with ethyl acetate (50 mL)
7. washThe filtrate was washed with water and brine
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by column chromatography (Biotage, 40 M; 20% ethyl acetate:hexanes)