反应详情

Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3.8 g, 17 mmol) was dissolved in phosphorus oxychloride (25 mL, 0.26 mol, 15 equiv) and stirred at ambient temperature for 14 hours. The mixture was concentrated in vacuo and the residue was concentrated from toluene (3×25 mL). The resulting residue was dissolved in 1,2-dimethoxyethane (60 mL) and degassed N,N-dimethylformamide (10 mL) and treated with 2-fluorophenylhydrazine (4.4 g, 35 mmol, 2 equiv) and potassium carbonate (12 g, 87 mmol, 5 equiv). The mixture was placed into a preheated oil bath at 80° C. for 14 hours. The mixture was cooled to ambient temperature, diluted with water (100 mL) and ethyl acetate (100 mL) and filtered. The solid was collected and dried in vacuo, providing the titled compound as a yellow solid.

1. concentrationThe mixture was concentrated in vacuo
2. concentrationthe residue was concentrated from toluene (3×25 mL)
3. dissolutionThe resulting residue was dissolved in 1,2-dimethoxyethane (60 mL)
4. customdegassed N,N-dimethylformamide (10 mL)
5. waitThe mixture was placed into a preheated oil bath at 80° C. for 14 hours
6. temperatureThe mixture was cooled to ambient temperature
7. filtrationfiltered
8. customThe solid was collected
9. customdried in vacuo