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

HRID 2167242Notes

Reaction equation

HRID 2167242 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

[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.

Workup

  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

Sources & evidence

ORD record
ord-458a7fa6ca6e4f31889d2c81fb1c54b5
Source dataset
uspto-grants-2015_06
Patent number
US09045423B2

Reaction notes

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