반응 #591180

반응 방정식

5-(1,3-Dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one

iodobenzene

trans-1,2-diaminocyclohexane

cesium carbonate

→

5-(1,3-dioxolan-2-yl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one

수율 93.8%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   온도under reflux for three days
2. 2
   온도After cooling
3. 3
   여과the insoluble matter was filtered off through a Celite pad
4. 4
   workup.ADDITIONEthyl acetate and water were added to the filtrate
5. 5
   세척the resulting mixture was washed (twice with water
6. 6
   건조once with a saturated sodium chloride solution), dried (MgSO4)
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1)

실험 절차

5-(1,3-Dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (2.30 g, 10.5 mmol), iodobenzene (3.5 ml, 31.5 mmol), copper(I) iodide (400 mg, 2.10 mmol), trans-1,2-diaminocyclohexane (0.129 ml, 1.05 mmol) and cesium carbonate (6.84 g, 21.0 mmol) were stirred in 30 ml of 1,4-dioxane under reflux for three days. After cooling, the insoluble matter was filtered off through a Celite pad. Ethyl acetate and water were added to the filtrate, and the resulting mixture was washed (twice with water and once with a saturated sodium chloride solution), dried (MgSO4), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3→1:1) to thereby obtain 2.91 g (yield: 92%) of 5-(1,3-dioxolan-2-yl)-1-phenyl-3,4-dihydro-1H-quinolin-2-one as a white solid.

출처