Phenol, 4-amino-, 1-acetate → 1-Acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinoline

HRID 1629668

반응식

HRID 1629668 반응식
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=O)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2].[C:16]([O:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)(=[O:18])[CH3:17]>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[N:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][C:16](=[O:18])[CH3:17])=[CH:26][CH:25]=2)[CH2:6][CH:5]1[CH3:15])(=[O:3])[CH3:2]

참가 물질

5

반응물 2

HCID 83783Phenol, 4-amino-, 1-acetateHCID 5895634(1H)-Quinolinone, 1-acetyl-2,3-dihydro-2-methyl-

생성물 1

HCID 666259871-Acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinoline수율 30.2%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 1140Toluene용매

실험 절차

[Step 1] 100 mg of 1-acetyl-4-oxo-2-methyl-1,2,3,4-tetrahydroquinoline and 227 mg of 4-acetoxyaniline were dissolved in 3 mL of toluene, and 250 μL of titanium tetrachloride (1.0 M dichloromethane solution) was added to the solution under ice cooling. The mixture was stirred for one hour under ice cooling, and then was stirred for another one hour at room temperature. After completion of the reaction, the reaction liquid was filtered through Celite and was concentrated under reduced pressure. The resulting residue was purified by using silica gel chromatography (chloroform), and thus 50 mg (30%) of 1-acetyl-2-methyl-4-[(4-acetoxyphenyl)imino]-1,2,3,4-tetrahydroquinoline was obtained as a yellow soup-like substance.

후처리

  1. stirringwas stirred for another one hour at room temperature
  2. customAfter completion of the reaction
  3. customthe reaction liquid
  4. filtrationwas filtered through Celite
  5. concentrationwas concentrated under reduced pressure
  6. customThe resulting residue was purified

출처 및 근거

ORD 기록
ord-e74c9e2b9678404b9d9f4d82316f3a1b
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791090B2

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