反应详情

DDQ (0.38 g, 1.7 mmol) was added to a solution of 6-fluoro-3,4-dihydro-1H-quinolin-2-one (0.18 g, 1.1 mmol) in dioxane (25 mL) and the resulting solution was refluxed for 16 h. The mixture was concentrated, and sat aqueous Na2CO3 (25 mL) was added followed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL). The combined organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and purified by flash CC (SiO2; CH2Cl2/MeOH 20:1) to give the title compound (0.056 g, 31%). 1H NMR (DMSO-D6) δ 11.8 (brs, 1H), 7.85 (d, J=9.4 Hz), 7.50 (dd, J=2.8, 9.2 Hz), 7.43-7.37 (m, 1H), 7.37-7.25 (m, 1H), 6.54 (d, J=9.4 Hz).

1. temperaturethe resulting solution was refluxed for 16 h
2. concentrationThe mixture was concentrated
3. additionwas added
4. extractionfollowed by extraction into an organic mixture (MeOH:CH2Cl2; 1:10, 3×50 mL)
5. dry with materialThe combined organic phase was dried (Na2SO4)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. custompurified by flash CC (SiO2; CH2Cl2/MeOH 20:1)