반응 #41923

반응 방정식

Tetraethylammonium

Ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

→

ethyl 2-(6-cyano-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

수율 90.0%

용매

1,4-dioxane

1,4-dioxane

반응 조건

후처리

1. 1
   기타the tube was sealed
2. 2
   온도After cooling
3. 3
   여과the mixture was filtered
4. 4
   세척washed with methylene chloride (50 ml)
5. 5
   세척The filtrate was washed with deionized water (3×50 ml)
6. 6
   건조with brine (50 ml), dried over magnesium sulfate
7. 7
   농축then concentrated
8. 8
   기타dried in vacuo
9. 9
   기타Flash column chromatography (Silica gel, 0-100% methylene chloride in hexane) gave a solid which
10. 10
    세척washed with diethyl ether
11. 11
    여과filtered
12. 12
    기타dried in vacuo

실험 절차

Ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.200 g, 0.46 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.048 g, 0.087 mmol), Copper cyamide (0.194 g, 2.2 mmol) and Tris(dibenzylideneacetone)dipalladium (0.020 g, 0.022 mmol) in 1,4-dioxane (2 ml) were combined in a 10 ml tube. Tetraethylammonium cyamide (0.085 g, 0.54 mmol) and 1,4-dioxane (1 ml) were added and the tube was sealed and heated to 145° C. for 15 min under Argon in a microwave (Personal Chemistry 300 W). After cooling, the mixture was filtered and washed with methylene chloride (50 ml). The filtrate was washed with deionized water (3×50 ml), then with brine (50 ml), dried over magnesium sulfate then concentrated and dried in vacuo. Flash column chromatography (Silica gel, 0-100% methylene chloride in hexane) gave a solid which washed with diethyl ether, filtered and dried in vacuo to give ethyl 2-(6-cyano-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.135 g, 90% yield).

출처