反应详情

Into a 500 mL three-neck flask equipped with a condenser, magnetic stirrer, nitrogen inlet gas outlet and a silicone oil heating bath was placed 4-azido-2-(3-fluorophenyl)-6-nitro-quinoline. The material was suspended in 250 mL of ethyl acetate and 50 mL of ethanol. The stirred mixture was heated to reflux, then 20 g (89 mmoles, 6 equiv.) of stannous chloride dihydrate was cautiously added portionwise over 40 min. The reaction was then heated for an additional 2 hr. At the end of this time, the reaction was cooled and then poured into 500 mL of water. The pH was cautiously adjusted to 9.0 and the solution filtered. The solids were washed with 100 mL of ethyl acetate, the filtrates combined and the aqueous layer extracted twice with 200 mL of ethyl acetate. The organic layers were combined, dried over Na2SO4, filtered and concentrated. The product was chromatographed on a silica gel column, using 10% methanol in ethyl acetate as eluent, and was then recrystallised from methylene chloride and hexane to give 3.6 g (88%) of the product.

1. customInto a 500 mL three-neck flask equipped with a condenser, magnetic stirrer, nitrogen inlet gas outlet and a silicone oil heating bath
2. temperatureThe stirred mixture was heated
3. temperatureto reflux
4. temperatureThe reaction was then heated for an additional 2 hr
5. temperatureAt the end of this time, the reaction was cooled
6. filtrationthe solution filtered
7. washThe solids were washed with 100 mL of ethyl acetate
8. extractionthe aqueous layer extracted twice with 200 mL of ethyl acetate
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe product was chromatographed on a silica gel column
13. customwas then recrystallised from methylene chloride and hexane