反应详情

N-(2-Fluorophenyl)cinnamamide (10.5 g, 44 mmol) was dissolved in chlorobenzene (60 mL) and aluminum trichloride (29 g, 218 mmol, 5 eq) was added. The reaction was heated to 125 C for 3 h and then cooled to rt over 45 minutes. The reaction was poured onto 300 g of ice with stirring, producing a tan solid. The solid was filtered and washed with 100 mL of water and 3×100 mL of hexanes and dried under high vacuum. The solid was extracted with 1 L of DCM and filtered to remove insoluble byproducts. The solvent was removed in vacuo to afford 8-fluoroquinolin-2(1H)-one. 1H NMR (400 MHz, CDCl3) δ ppm 10.95 (br s, 1H), 7.77 (dd, J=9.8, 1.6 Hz), 7.35 (d, J=7.8 Hz, 1H), 7.27 (ddd, J=10.2, 7.8, 1.2 Hz, 1H), 7.14 (td, J=8.0, 5.1 Hz, 1H), 6.76 (d, J=9.4 Hz, 1H).

1. temperatureThe reaction was heated to 125 C for 3 h
2. customproducing a tan solid
3. filtrationThe solid was filtered
4. washwashed with 100 mL of water and 3×100 mL of hexanes
5. customdried under high vacuum
6. extractionThe solid was extracted with 1 L of DCM
7. filtrationfiltered
8. customto remove insoluble byproducts
9. customThe solvent was removed in vacuo