반응 #591174

반응 방정식

8-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

ethylene glycol

sodium bicarbonate

→

5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one

수율 70.0%

용매

toluene

반응 조건

후처리

1. 1
   온도the resulting mixture was heated
2. 2
   온도under reflux in a Dean-Stark apparatus for 4.5 hours
3. 3
   온도The reaction mixture was cooled
4. 4
   workup.ADDITIONwas added
5. 5
   여과the produced solid was collected by filtration
6. 6
   세척The solid was washed with water and toluene
7. 7
   기타dried at 60° C.

실험 절차

8-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (42 g) was suspended in toluene (400 ml), and ethylene glycol (33.7 ml) and p-toluenesulfonic acid monohydrate (0.78 g) were added, and the resulting mixture was heated under reflux in a Dean-Stark apparatus for 4.5 hours. The reaction mixture was cooled, and 10 ml of an aqueous solution containing 1.72 g of sodium bicarbonate was added. Stirring was carried out for some time, and the produced solid was collected by filtration. The solid was washed with water and toluene and dried at 60° C. to thereby obtain 35.5 g (yield: 70%) of 5-(1,3-dioxolan-2-yl)-8-methoxy-3,4-dihydro-1H-quinolin-2-one as white crystals.

출처