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

HRID 503983노트

반응식

HRID 503983 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9][CH2:8]2.[CH3:14][O:15]C(Cl)Cl>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[CH2:9][CH2:8][C:7]=2[C:6]([CH:14]=[O:15])=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 21004Methane, dichloromethoxy-HCID 133754763,4-Dihydro-8-methoxy-2(1H)-quinolinone

생성물 1

HCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde수율 90%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

8-Methoxy-3,4-dihydro-1H-quinolin-2-one (5 g) was dissolved in dichloromethane (100 ml), and dichloromethyl methyl ether (6.4 ml) was added at room temperature, followed by cooling in an ice water bath. Titanium tetrachloride (85 ml) was added dropwise at a temperature not higher than 10° C., and the resulting mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water, and the aqueous layer was subjected to extraction with dichloromethane. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Diethyl ether was added to the residue and the produced solid was collected by filtration and dried to thereby obtain 5.2 g (yield: 90%) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde.

후처리

  1. temperatureby cooling in an ice water bath
  2. extractionthe aqueous layer was subjected to extraction with dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionDiethyl ether was added to the residue
  7. filtrationthe produced solid was collected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-6c478eca850d490e8b23feba2869626a
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07777038B2

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