反应详情

温度

80 °C

To an ice-cold solution of 3-(1-amino-2-naphthylamino)benzonitrile (968 mg, 3.73 mmol) in toluene (10 mL) was added malonyl chloride (436 μL, 4.48 mmol). The mixture was stirred at 80° C. for 20 minutes, then at 110° C. for 10 minutes. After the reaction mixture was cooled to room temperature, the solution part of the reaction mixture was poured into a saturated aqueous sodium bicarbonate solution, and was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. While The precipitated solid in the reaction mixture was dissolved in chloroform, was washed with a saturated aqueous sodium bicarbonate solution, and saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed under reduced pressure. The residues were combined, and Each product purified by silica gel column chromatography (hexane/ethyl acetate=1/4), and the residue was recrystallized from ethyl acetate to give the titled compound as a pale yellow crystal (335 mg, yield 27%). mp: 220-222° C.

1. waitat 110° C. for 10 minutes
2. temperatureAfter the reaction mixture was cooled to room temperature
3. extractionwas extracted with ethyl acetate
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. customthe solvent was removed under reduced pressure
6. dissolutionWhile The precipitated solid in the reaction mixture was dissolved in chloroform
7. washwas washed with a saturated aqueous sodium bicarbonate solution, and saturated brine
8. dry with materialAfter drying over anhydrous sodium sulfate
9. customthe solvent was removed under reduced pressure
10. customEach product purified by silica gel column chromatography (hexane/ethyl acetate=1/4)
11. customthe residue was recrystallized from ethyl acetate