反应详情

A mixture of 6-fluoroquinoline (2 g, 13.6 mmol) and fuming HNO3 (15 mL) in a round bottom flask equipped with a cooling condenser was refluxed for 100 hours, the resulting mixture was cooled to r.t., poured slowly into crushed ice/H2O, and then the mixture was extracted with DCM (200 mL×3). The combined organic layers were dried over Na2SO4, and concentrated. The residue was passed through a short pad of silica gel to give 1.6 g of title compound. 1H NMR (CHLOROFORM-d) δ: 9.08 (dd, J=4.1, 1.5 Hz, 1H), 8.25 (dd, J=8.5, 1.5 Hz, 1H), 7.89 (dd, J=7.5, 2.8 Hz, 1H), 7.72 (dd, J=8.1, 2.8 Hz, 1H), 7.62 (dd, J=8.4, 4.3 Hz, 1H). LC-MS: m/z 466.6 (M+H)+

1. customequipped with a cooling condenser
2. temperaturewas refluxed for 100 hours
3. additionpoured slowly
4. extractionthe mixture was extracted with DCM (200 mL×3)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. concentrationconcentrated