反应详情

Ethyl 1-[(2-fluoro-4-iodophenyl)methyl]-4-oxo-1,4-dihydroquinoline-3-carboxylate (1.4 g, 3.1 mmol) was dissovled in phosphorus oxychloride (6.0 mL, 64 mmol, 21 equiv) and stirred for 2.5 hours at ambient temperature. The mixture was diluted with toluene (10 mL) and concentrated in vacuo. The residue was dissolved in dioxane (17 mL), treated with 2-fluorophenylhydrazine (0.87 g, 6.8 mmol, 2.2 equiv) and potassium carbonate (1.3 g, 9.4 mmol, 3 equiv) and stirred at ambient temperature for 5 minutes. The mixture was placed into a preheated oil bath at 80° C. for 1 hour, cooled to ambient temperature and diluted with chloroform (150 mL). The organic mixture was washed once with water (50 mL) and brine (50 mL), dried with sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with a chloroform:methanol (95:5) solution (30 mL). The solid was filtered and dried in vacuo, providing the titled compound.

1. concentrationconcentrated in vacuo
2. dissolutionThe residue was dissolved in dioxane (17 mL)
3. stirringstirred at ambient temperature for 5 minutes
4. waitThe mixture was placed into a preheated oil bath at 80° C. for 1 hour
5. temperaturecooled to ambient temperature
6. washThe organic mixture was washed once with water (50 mL) and brine (50 mL)
7. dry with materialdried with sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was triturated with a chloroform:methanol (95:5) solution (30 mL)
11. filtrationThe solid was filtered
12. customdried in vacuo