反应详情

A mixture of 356.2 mg (1.3 mmol) of 7,8-dimethoxy-4-oxo-1,4-dihydrobenzo[g]quinoline-3-carbonitrile in 5 mL of phosphorus oxychloride and 4 drops of DMF is heated at 100–110° C. for 4.5 hours. After cooling, the mixture is concentrated to dryness in vacuo to give a dark residue. The residue is partitioned between methylene chloride and ice-cooled saturated aqueous sodium carbonate solution. The organic layer is washed with cooled brine and dried over sodium sulfate. The organic solvent is passed through a short column of silica gel, and the column is first eluted with additional methylene chloride, then a 99:1 methylene chloride/ethyl acetate solution. Removal of the solvent yields 187.0 mg (49.4%) of the product as a bright yellow solid, mp>265° C.

1. temperatureis heated at 100–110° C. for 4.5 hours
2. temperatureAfter cooling
3. concentrationthe mixture is concentrated to dryness in vacuo
4. customto give a dark residue
5. customThe residue is partitioned between methylene chloride and ice-
6. temperaturecooled saturated aqueous sodium carbonate solution
7. washThe organic layer is washed with cooled brine
8. dry with materialdried over sodium sulfate
9. washthe column is first eluted with additional methylene chloride
10. customRemoval of the solvent