반응 #43397

반응 방정식

8-[1-(chloromethyl)ethenyl]-7-fluoro-2-(methyloxy)-1,5-naphthyridine

sodium iodide

→

solid

수율 36.0%

3-Fluoro-4-methylidene-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

수율 36.0%

용매

ethyl acetate

acetone

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도to reflux for 18 hours
3. 3
   기타The mixture was evaporated
4. 4
   기타the residue partitioned between water (200 ml) and dichloromethane (200 ml)
5. 5
   추출The aqueous phase was further extracted with dichloromethane (2×200 ml)
6. 6
   세척the combined dichloromethane extracts washed with water (2×200 ml)
7. 7
   건조dried over magnesium sulphate
8. 8
   기타evaporated
9. 9
   기타The resulting solid was triturated with ethyl acetate (50 ml)
10. 10
    여과filtered
11. 11
    세척washed with ethyl acetate (20 ml)
12. 12
    기타affording a brown solid
13. 13
    여과filtered through a plug of silica
14. 14
    기타Evaporation

실험 절차

A mixture of 8-[1-(chloromethyl)ethenyl]-7-fluoro-2-(methyloxy)-1,5-naphthyridine (4.9 g, 19.5 mmol) and sodium iodide (29 g, 195 mmol) in acetone (100 ml) was heated to reflux for 18 hours. The mixture was evaporated and the residue partitioned between water (200 ml) and dichloromethane (200 ml). The aqueous phase was further extracted with dichloromethane (2×200 ml) and the combined dichloromethane extracts washed with water (2×200 ml) dried over magnesium sulphate and evaporated. The resulting solid was triturated with ethyl acetate (50 ml) and filtered and washed with ethyl acetate (20 ml) affording a brown solid. This material was then dissolved in ethyl acetate and filtered through a plug of silica. Evaporation afforded a solid (1.4 g, 36%).

출처