반응 #591197

반응 방정식

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

N-methylaniline

potassium carbonate

acetonitrile

→

5-(1,3-dioxolan-2-yl)-1-(4-[(N-methyl-N-phenylamino)methyl]benzyl)-3,4-dihydro-1H-quinolin-2-one

수율 67.0%

용매

dichloromethane

water

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도under reflux for 4 hours
3. 3
   세척The organic layer was washed with water
4. 4
   건조a saturated sodium chloride solution, and dried over anhydrous sodium sulfate
5. 5
   농축The dry product was concentrated under reduced pressure
6. 6
   기타the residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1)
7. 7
   농축The purified product was concentrated to dryness under reduced pressure

실험 절차

1-(4-Chloromethylbenzyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (100 mg, 0.28 mmol), N-methylaniline (0.045 ml, 0.42 mmol) and potassium carbonate (57.9 mg, 0.42 mmol) were added to acetonitrile (1 ml), followed by heating under reflux for 4 hours. After cooling to room temperature, water was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The dry product was concentrated under reduced pressure, and the residue was purified by preparative silica gel thin layer chromatography (n-hexane:ethyl acetate=1:1). The purified product was concentrated to dryness under reduced pressure to thereby obtain 80 mg (yield: 67%) of 5-(1,3-dioxolan-2-yl)-1-(4-[(N-methyl-N-phenylamino)methyl]benzyl)-3,4-dihydro-1H-quinolin-2-one as a light yellow amorphous solid.

출처