反应详情

A mixture of 2,3-dihydro-thiopyrano[2,3-b]pyridin-4-one (2.24 g, 13.6 mmoL) and 4-methoxy-phenylhydrazine HCl salt (2.60 g, 14.9 mmoL) in EtOH (10 mL) was refluxed for 5 hours. The reaction mixture was cooled and filtrated through a pad of Celite to remove any solids in the mixture. The solvent was removed in vacuo. The remaining residue was partitioned between EtOAc and saturated NaHCO3. The aqueous phase was extracted two times with EtOAc. The organic layer of each extraction was washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was, then purified by column chromatography (silica gel, hexanes: EtOAc1:1 as eluent) to yield the title compound as a pale solid.

1. temperaturewas refluxed for 5 hours
2. temperatureThe reaction mixture was cooled
3. filtrationfiltrated through a pad of Celite
4. customto remove any solids in the mixture
5. customThe solvent was removed in vacuo
6. customThe remaining residue was partitioned between EtOAc and saturated NaHCO3
7. extractionThe aqueous phase was extracted two times with EtOAc
8. extractionThe organic layer of each extraction
9. washwas washed with water, brine
10. dry with materialdried over anhydrous Na2SO4
11. filtrationfiltered
12. concentrationconcentrated
13. customto yield a brown oil
14. custompurified by column chromatography (silica gel, hexanes: EtOAc1:1 as eluent)