反应详情

A mixture of 7-fluoro-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone (5.25 g), sodium cyanide (1.0 g), crown ether (18-crown-6, 5.4 g) and acetonitrile (200 ml) was stirred and boiled under reflux for 79 hours, left at ambient temperature for 70 hours, and boiled under reflux for 24 hours. The mixture was cooled and filtered. The residue was boiled with industrial methylated spirit (200 ml) and the mixture filtered while hot. The residue was further extracted twice with boiling 50% aqueous industrial methylated spirit (400 ml, then 200 ml). Each hot extract precipitated a solid when cooled. The three solids were combined and recrystallised from 50% aqueous industrial methylated spirit to give a crude product. This product was purified by high pressure liquid chromatography on silica, using dichloromethane:methanol 9:1 as the eluent. The eluent was evaporated to give a residue which was recrystallised from 30% aqueous industrial methylated spirit to give the novel compound 7-cyano-1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-quinolone, m.p. 301°-303°.

1. temperatureunder reflux for 79 hours
2. temperatureunder reflux for 24 hours
3. temperatureThe mixture was cooled
4. filtrationfiltered
5. filtrationthe mixture filtered while hot
6. extractionThe residue was further extracted twice
7. extractionEach hot extract
8. customprecipitated a solid when
9. temperaturecooled
10. customrecrystallised from 50% aqueous industrial methylated spirit
11. customto give a crude product
12. customThis product was purified by high pressure liquid chromatography on silica
13. customThe eluent was evaporated
14. customto give a residue which
15. customwas recrystallised from 30% aqueous industrial methylated spirit