反応 #43397

反応方程式

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

sodium iodide

→

solid

収率 36.0%

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

収率 36.0%

溶媒

ethyl acetate

acetone

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度to reflux for 18 hours
3. 3
   その他The mixture was evaporated
4. 4
   その他the residue partitioned between water (200 ml) and dichloromethane (200 ml)
5. 5
   抽出The aqueous phase was further extracted with dichloromethane (2×200 ml)
6. 6
   洗浄the combined dichloromethane extracts washed with water (2×200 ml)
7. 7
   乾燥dried over magnesium sulphate
8. 8
   その他evaporated
9. 9
   その他The resulting solid was triturated with ethyl acetate (50 ml)
10. 10
    ろ過filtered
11. 11
    洗浄washed with ethyl acetate (20 ml)
12. 12
    その他affording a brown solid
13. 13
    ろ過filtered through a plug of silica
14. 14
    その他Evaporation

実験手順

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%).

出典