反应详情

To a solution of 3-(trifluoromethyl)aniline (12.43 mL, 99.92 mmol) in 6 N HCl (50 mL) in water was added (E)-but-2-enal (18.77 mL, 229.8 mmol) dropwise at reflux. The reaction was stirred at reflux for 3 hours. After cooling to ambient temperature, ethyl acetate (200 mL) was added. The aqueous layer was separated, basified with ammonium hydroxide to about pH 9, and extracted with DCM (2×200 mL). The combined organic layers were dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give 2-methyl-7-(trifluoromethyl)quinoline (6.1 g, 28.9%) as a solid.

1. temperatureat reflux
2. temperatureat reflux for 3 hours
3. customThe aqueous layer was separated
4. extractionextracted with DCM (2×200 mL)
5. dry with materialThe combined organic layers were dried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)