반응 #591177

반응 방정식

Pyridinium p-toluene sulfonate

5-(1,3-dioxolan-2-yl)-8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-3,4-dihydro-1H-quinolin-2-one

sodium hydrogencarbonate

ethyl acetate

→

8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

수율 81.0%

용매

acetone

water

반응 조건

후처리

1. 1
   온도by heating
2. 2
   온도under reflux for 2 hours
3. 3
   세척The extract was washed twice with water
4. 4
   세척washed with a saturated sodium chloride solution
5. 5
   건조dried over sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
9. 9
   농축The purified product was concentrated under reduced pressure

실험 절차

Pyridinium p-toluene sulfonate (PPTS) (0.54 g) was added to a mixed solution of 5-(1,3-dioxolan-2-yl)-8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-3,4-dihydro-1H-quinolin-2-one (0.95 g) in acetone (19 ml) and water (9.5 ml), followed by heating under reflux for 2 hours. An aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed twice with water, washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1). The purified product was concentrated under reduced pressure to thereby obtain 0.69 g (yield: 81%) of 8-methoxy-1-[6-(N-methyl-N-phenylamino)pyridin-3-ylmethyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a light yellow amorphous solid.

출처