Azobisisobutyronitrile → 3-Benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline

HRID 1684574Notes

Reaction equation

HRID 1684574 reaction equation
[C:1]([C:9]1[C:10]([CH3:33])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:34]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:9]1[C:10]([CH2:33][Br:34])=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=1)=[CH:16][C:15]([O:29][CH3:30])=[C:14]([O:31][CH3:32])[CH:13]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19039879HCID 19039879, compound

Product 1

HCID 190399113-Benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinolineYield 42.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-benzoyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline (5.5 g), N-bromosuccinimide (2.42 g), 2,2'-azobis(isobutyronitrile)(0.815 g) and carbon tetrachloride (250 ml) was stirred under reflux for 1.5 hours. The reaction mixture was cooled, and then the insoluble material was filtered off. The filtrate was washed with water and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel. The fractions eluted with chloroform-ethyl acetate (10:1, v/v) gave 3-benzoyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (2.73 g, 42%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 182°-183° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe insoluble material was filtered off
  4. washThe filtrate was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. washThe fractions eluted with chloroform-ethyl acetate (10:1

Sources & evidence

ORD record
ord-169bdaf4e5164459a3bc533f19ae0dce
Source dataset
uspto-grants-1997_06
Patent number
US05641788

Reaction notes

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