反应详情

To a mixture of 1.8 g of ethyl 4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-3-nitrobenzoate, 32 ml of ethanol and 32 ml of tetrahydrofuran was added 640 mg of 10% palladium/carbon under an argon atmosphere, followed by 2 hours of stirring at room temperature under a hydrogen atmosphere. The reaction solution was filtrated through celite and the organic solvent in the filtrate was removed under reduced pressure. To the residue were added 50 ml of methanol and 2 drops of concentrated hydrochloric acid, followed by 30 minutes of stirring at 60° C. After cooling to room temperature, the reaction solution was concentrated under reduced pressure and water and chloroform were added to the residue, followed by an analytical operation. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed by evaporation. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate) to obtain 1.16 g of ethyl 2-oxo-1,2,3,4-tetrahydroquinoline-7-carboxylate as a white solid.

1. filtrationThe reaction solution was filtrated through celite
2. customthe organic solvent in the filtrate was removed under reduced pressure
3. additionTo the residue were added 50 ml of methanol and 2 drops of concentrated hydrochloric acid
4. waitfollowed by 30 minutes
5. stirringof stirring at 60° C
6. temperatureAfter cooling to room temperature
7. concentrationthe reaction solution was concentrated under reduced pressure and water and chloroform
8. additionwere added to the residue
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. customthe solvent was removed by evaporation
11. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate)