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