反应详情

To a solution of 6.30 g (30.3 mmol) 6-chloro-8-nitroquinoline, 14.7 g (272 mmol) NH4Cl, 120 mL H2O and 250 mL EtOH is added 5.0 g (90.6 mmol) Fe powder, and the resulting mixture is refluxed for 2.5 h. The volatiles are evaporated, and the residue is stirred in mixture of 200 mL CH2Cl2 and 300 mL water for 30 min. The resulting bi-phasic solution is filtered through celite, the layers are separated, and the aqueous layer is extracted 2×100 mL CH2Cl2. The combined organics are washed with 1×100 mL H2O, 1×100 mL brine, dried over MgSO4, filtered, and the volatiles are evaporated. Flash chromatography on SiO2, eluting with hexanes/EtOAC (10/1 to 4/1), gives 2.80 g (15.7 mmol, a 52% yield) of the title compound as a tan solid. mp: 70-73° C.; MS (ES) m/z 179 (MH)+.

1. temperaturethe resulting mixture is refluxed for 2.5 h
2. customThe volatiles are evaporated
3. filtrationThe resulting bi-phasic solution is filtered through celite
4. customthe layers are separated
5. extractionthe aqueous layer is extracted 2×100 mL CH2Cl2
6. washThe combined organics are washed with 1×100 mL H2O, 1×100 mL brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. customthe volatiles are evaporated
10. washFlash chromatography on SiO2, eluting with hexanes/EtOAC (10/1 to 4/1)
11. customgives 2.80 g (15.7 mmol