反应详情

温度

70 °C

To a solution of 6-chloro-3-methyl-5-(2,2,2-trichloro-ethyl)isoquinoline (3.3 g, 10.7 mmol) in anhydrous methanol (64 mL) was added a 30% solution of NaOMe in methanol (9.6 mL) under an argon atmosphere. The resulting brown solution was heated for 3 h at 70° C. After cooling to 0° C., concentrated H2SO4 (5.7 mL) was carefully added and the resulting reaction mixture was heated for 1 h at 70° C. After cooling the reaction mixture was rendered basic (pH=9) with a saturated aqueous NaHCO3 solution and extracted three times with diethyl ether. The combined organic layers were dried over Na2SO4, filtered and concentrated at reduced pressure to afford a brown solid. Purification by flash column chromatography (silica gel, cyclohexane/ethyl actetate 70:30) afforded the title compound as a brown powder (1.91 g, 7.63 mmol, 70%). MS (ES+): 250 (M(C13H1235ClNO2)+H)+.

1. temperatureAfter cooling to 0° C.
2. customthe resulting reaction mixture
3. temperaturewas heated for 1 h at 70° C
4. temperatureAfter cooling the reaction mixture
5. extractionextracted three times with diethyl ether
6. dry with materialThe combined organic layers were dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated at reduced pressure
9. customto afford a brown solid
10. customPurification by flash column chromatography (silica gel, cyclohexane/ethyl actetate 70:30)