反应详情

温度

90 °C

7-Chloro4-quinolinol (2 g, 11.1 mmol), Li2CO3 (1.7 g, 22.3 mmol) and NMP (16 mL) were charged in a 100 ml round-bottomed flask equipped with a magnetic stirrer. 1,5-Dibromopentane (13.5 g, 55.7 mmol) was added and the reaction mixture was stirred for 1 h at 90° C. The reaction mixture was poured in 100 mL of H2O, extracted with EtOAc (300 mL). The organic layer was washed with water (30 mL), brine (2×30 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. HCl 1M in diethyl ether (15 mL, 15 mmol) was added and the bis-alkylated product was precipitated and filtered. The precipitate was dissolved in water with K2CO3 (1.5 g, 11.1 mmol), extracted with EtOAc (300 mL). The organic layer was washed with brine (2×20 mL), dried over MgSO4, filtered and evaporated at 30° C. to dryness. The crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 95:5) to give after evaporation 4-(5-bromopentyloxy)-7-chloroquinoline 33 (0.45 g, 12% yield) as a white solid.

1. customequipped with a magnetic stirrer
2. extractionextracted with EtOAc (300 mL)
3. washThe organic layer was washed with water (30 mL), brine (2×30 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated at 30° C. to dryness
7. customthe bis-alkylated product was precipitated
8. filtrationfiltered
9. extractionextracted with EtOAc (300 mL)
10. washThe organic layer was washed with brine (2×20 mL)
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. customevaporated at 30° C. to dryness
14. customThe crude compound was purified by column chromatography (SiO2; CH2Cl2:MeOH=99.5:0.5 to 95:5)
15. customto give