反应详情

温度

150 °C

After suspending 7-benzyloxy-6-cyano-4-chloroquinoline (23 g, 78.03 mmol) in N-methylpyrrolidone (15.8 ml), there were added 5-hydroxyindole (12.5 g, 83.64 mmol) and diisopropylethylamine (15.8 ml) and the mixture was heated and stirred at 150° C. for 10 hours. After allowing it to cool to room temperature, water and tetrahydrofuran were added and the crystals were thoroughly dissolved. After extraction with tetrahydrofuran, washing with saturated saline, drying over anhydrous magnesium sulfate and distilling off of the solvent, the residue was adsorbed onto silica gel. Purification was performed by silica gel column chromatography (hexane/tetrahydrofuran system), and then concentrated hydrochloric acid (0.2 ml) was added at room temperature and the mixture was stirred for 17 hours. The solvent was distilled off under reduced pressure, saturated bicarbonate water was added, and then extraction was performed with a tetrahydrofuran and ethyl acetate mixed solvent, the extract was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crystals were suspended in ethyl acetate and diluted with diethyl ether and hexane. The crystals were filtered out, washed with diethyl ether/hexane and dried by aspiration to obtain the title compound (12.5 g, 31.93 mmol, 40.92%) as light yellow crystals.

1. temperaturethe mixture was heated
2. temperatureto cool to room temperature
3. dissolutionthe crystals were thoroughly dissolved
4. extractionAfter extraction with tetrahydrofuran
5. washwashing with saturated saline
6. dry with materialdrying over anhydrous magnesium sulfate
7. distillationdistilling off of the solvent
8. customPurification
9. additionconcentrated hydrochloric acid (0.2 ml) was added at room temperature
10. stirringthe mixture was stirred for 17 hours
11. distillationThe solvent was distilled off under reduced pressure, saturated bicarbonate water
12. additionwas added
13. extractionextraction
14. washthe extract was washed with saturated saline
15. dry with materialdried over anhydrous magnesium sulfate
16. distillationthe solvent was distilled off under reduced pressure
17. additiondiluted with diethyl ether and hexane
18. filtrationThe crystals were filtered out
19. washwashed with diethyl ether/hexane
20. customdried by aspiration