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

HRID 1684571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1684571
[C:1]([C:4]1[C:5]([CH3:28])=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2].[Br:29]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:4]1[C:5]([CH2:28][Br:29])=[N:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)=[CH:11][C:10]([O:24][CH3:25])=[C:9]([O:26][CH3:27])[CH:8]=2)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 190398893-Acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline

Produkt 1

HCID 190399053-Acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinolineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 3-acetyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline (8.5 g), N-bromosuccinimide (5. mg) , 2,2'-azobis(isobutyronitrile) (1.46 g) and carbon tetrachloride (500 ml) was stirred under reflux for 40 minutes. 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 (20:1, v/v) gave 3-acetyl-2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline (6.85 g, 67%). This compound was recrystallized from ethyl acetate-hexane to give colorless prisms, mp. 181°-182° C.

Aufarbeitung

  1. temperatureunder reflux for 40 minutes
  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 (20:1

Quellen und Nachweise

ORD-Eintrag
ord-986475c4ad2749f992598d0af9718ddb
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05641788

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