反应详情

3-Fluoro-7-methoxyquinol-2(1H)-one (300 mg, 1.55 mmol), (prepared as in Tetrahedron, Vol. 52, No. 9, pp. 3223-3228, 1996), was dissolved in thionyl chloride (3 ml), treated with DMF (1 drop) and heated at reflux for 1 hour. The excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene (3×). The residue was basified to pH8 with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (3×20 ml). The organic solution was washed with water and brine then dried (MgSO4) and evaporated to dryness to give 2-chloro-3-fluoro-7-methoxyquinoline (320 mg, 97%).

1. temperatureheated
2. temperatureat reflux for 1 hour
3. customThe excess thionyl chloride was removed by evaporation
4. customthe residue azeotroped with toluene (3×)
5. extractionextracted with ethyl acetate (3×20 ml)
6. washThe organic solution was washed with water and brine
7. dry with materialthen dried (MgSO4)
8. customevaporated to dryness