反应详情

The mixture of 7-amino-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (1.07 g, 5.62 mmol) and borane dimethylsulfide complex (1.60 ml, 16.9 mmol) in 40 ml of anhydrous THF was heated at reflux under N2 for 15 h. The solvents were removed under reduced pressure. The residue was heated at reflux in 20 ml of MeOH for 2 h, then 0.80 g of NaHCO3 was added, and the mixture was heated at reflux for 2 h. The mixture was filtered, condensed, and the residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2). The titled compound was obtained as a viscous oil. MS (ES+): 176.9 (M+H)+. Calc'd for C11H16N—176.26.

1. temperaturewas heated
2. temperatureat reflux under N2 for 15 h
3. customThe solvents were removed under reduced pressure
4. temperatureThe residue was heated
5. temperatureat reflux in 20 ml of MeOH for 2 h
6. addition0.80 g of NaHCO3 was added
7. temperaturethe mixture was heated
8. temperatureat reflux for 2 h
9. filtrationThe mixture was filtered
10. customcondensed
11. customthe residue was purified by flash column chromatography (5 to 10% of EtOAc in CH2Cl2)