反应详情

Ethyl 4-oxo-1,4-dihydroquinoline-3-carboxylate (3.17 g, 14.6 mmol) and 4-methoxybenzylchloride (2.18 mL, 16.0 mmol, 1.1 equiv) were combined in N,N-dimethylformamide (50 mL) and stirred at ambient temperature for 72 hours. The mixture was poured into water (500 mL) and extracted with dichloromethane (2×250 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was treated with water (500 mL), hexanes (500 mL) and ethyl acetate (500 mL) and aged for 30 minutes. The mixture was filtered and the solid was dissolved in dichloromethane (500 mL) and combined with the filtrate. The filtrate was partitioned and the aqueous layer was discarded. The organic layer was dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

1. extractionextracted with dichloromethane (2×250 mL)
2. dry with materialThe combined organic extracts were dried with sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. additionThe residue was treated with water (500 mL), hexanes (500 mL) and ethyl acetate (500 mL)
6. waitaged for 30 minutes
7. filtrationThe mixture was filtered
8. dissolutionthe solid was dissolved in dichloromethane (500 mL)
9. customThe filtrate was partitioned
10. dry with materialThe organic layer was dried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated in vacuo