反应详情

温度

55 °C

Added DCM (2 mL) to 1-(2,5-dichloroquinolin-3-yl)ethanol (200 mg, 826 μmol). Added thionyl chloride (301 μl, 4131 μmol). Obtained a clear colorless solution within minutes. Concentrated reaction mixture to dryness on the rotavap to obtain an oil, which was used without further purification. LC-MS (+esi, M+H+=260.0). Dissolved 2,5-dichloro-3-(1-chloroethyl)quinoline (215 mg, 825 μmol) in DMF (2 mL) and added phthalimide (127 mg, 866 μmol) and K2CO3 (228 mg, 1650 μmol). Submerged in oil bath and began heating to 55° C. After 10 min the temperature of the oil bath was raised to 80° C. After 30 more minutes the reaction mixture was partitioned between EtOAc:H2O. The organic layer was washed with water (3×), dried with sodium sulfate, filtered, and concentrated. The crude was solid was chromatographed on 12 g silica gel column with 0-20% EtOAc:Hex. The desired fractions were combined and concentrated to yield a white crystalline solid. 1H NMR (400 MHz, DICHLOROMETHANE-d2) δ ppm 1.99 (d, J=7.04 Hz, 3 H) 5.93 (q, J=7.17 Hz, 1 H) 7.64-7.70 (m, 2 H) 7.71-7.76 (m, 2 H) 7.77-7.83 (m, 2 H) 7.88-7.93 (m, 1 H) 8.95 (s, 1 H). LC-MS (+esi, M+H+=371.0)

1. customObtained a clear colorless solution within minutes
2. concentrationConcentrated
3. customreaction mixture to dryness on the rotavap
4. customto obtain an oil, which
5. customwas used without further purification
6. customSubmerged in oil bath
7. temperatureAfter 10 min the temperature of the oil bath was raised to 80° C
8. customAfter 30 more minutes the reaction mixture was partitioned between EtOAc
9. washThe organic layer was washed with water (3×)
10. dry with materialdried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customwas chromatographed on 12 g silica gel column with 0-20% EtOAc
14. concentrationconcentrated
15. customto yield a white crystalline solid