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

HRID 1684571ノート

反応式

HRID 1684571 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-986475c4ad2749f992598d0af9718ddb
出典データセット
uspto-grants-1997_06
特許番号
US05641788

反応ノート

読み込み中…