反应详情

2.2 g (3.9 mmol) of (S)-N-(α-ethylbenzyl)-2-phenyl-3-(2-phthalimidoethoxy) quinoline-4-carboxamide (compound of Description 3) were dissolved in 150 ml of 96% EtOH; the solution was heated to reflux; 0.38 ml (7.8 mmol) of hydrazine hydrate were added and the reaction mixture refluxed for 4 hours. Additional 0.4 ml (8.2 mmol), 0.2 ml (4.1 mmol), 0.2 ml (4.1 mmol), 0.4 ml (8.2 mmol), 0.4 ml (8.2 mmol) of hydrazine hydrate were added every 12 hours while refluxing the reaction mixture. Then it was evaporated in-vacuo to dryness and 20 ml of H2O were added; it was cooled with an ice bath and 10 ml of conc. HCl were added. The reaction mixture was refluxed for 1 hour and then, after cooling, the phthalhydrazide was filtered off. The resulting aqueous filtrate was washed with EtOAc, basified with 2N NaOH and extracted with EtOAc. The organic layer was washed with sat. sol. NaCl, dried over Na2SO4 and evaporated in-vacuo to dryness. The residue was purified by flash column chromatography on 230-400 mesh silica gel, eluting with a mixture of EtOAc/MeOH 96:4 containing 1.2% NH4Oh (28%) to yield 1.2 g of the title compound.

1. temperaturethe solution was heated to reflux
2. temperaturethe reaction mixture refluxed for 4 hours
3. temperaturewhile refluxing the reaction mixture
4. customThen it was evaporated in-vacuo to dryness and 20 ml of H2O
5. additionwere added
6. temperatureit was cooled with an ice bath
7. addition10 ml of conc. HCl were added
8. temperatureThe reaction mixture was refluxed for 1 hour
9. temperatureafter cooling
10. filtrationthe phthalhydrazide was filtered off
11. washThe resulting aqueous filtrate was washed with EtOAc
12. extractionextracted with EtOAc
13. washThe organic layer was washed with sat. sol. NaCl
14. dry with materialdried over Na2SO4
15. customevaporated in-vacuo to dryness
16. customThe residue was purified by flash column chromatography on 230-400 mesh silica gel
17. washeluting with a mixture of EtOAc/MeOH 96:4 containing 1.2% NH4Oh (28%)