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

HRID 266116
ノート
印刷プレビュー

反応式

HRID 266116 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[C:13]([CH3:25])[C:12]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[Br:31]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:25][C:13]1[C:12]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:20]2[C:15](=[CH:16][C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=2)[N:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 19032371Ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate

生成物 1

HCID 21851143Ethyl 2-bromomethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate収率 58.2%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride
溶媒

実験手順

A mixture of ethyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxy-2-methylquinoline-3-carboxylate (411 mg), N-bromosuccinimide (214 mg), 2,2'-azobis(isobutyronitrile)(10 mg) and carbon tetrachloride (10 ml) was stirred under reflux for 5 hours. The reaction mixture 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 ethyl 2-bromomethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylate (285 mg, 58%). This compound was recrystallized from ethyl acetate-hexane. Colorless prisms, mp. 135°-136° C.

後処理

  1. temperatureunder reflux for 5 hours
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. washThe fractions eluted with chloroform-ethyl acetate (10:1

出典と根拠

ORDレコード
ord-41d0c1c736be4178b0006e76bb1d2a93
出典データセット
uspto-grants-1997_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05650410

反応ノート

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