O-Xylene → HCID 22132737、化合物

HRID 1857194ノート

反応式

HRID 1857194 の反応式
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.Cl[C:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:38][O:37][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][C:33]=1[O:39][CH3:40])[N:30]=[CH:29][CH:28]=[C:27]2[O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 7237O-XyleneHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 112298054-(4-hydroxybenzoyl)benzonitrile

生成物 1

HCID 22132737HCID 22132737、化合物収率 47.1%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

Under argon, 4-(4-hydroxybenzoyl)benzonitrile (230 mg) obtained in Example 123 and 4-dimethylaminopyridine (138 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (230 mg) was added, and the admixture was refluxed with heat for 20 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1) to obtain 199 mg of the title compound (yield: 47%).

後処理

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 20 hours
  3. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  4. dry with materialthe chloroform layer was then dried with anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. distillationby reduced-pressure distillation
  7. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-3caba43c70c54748946cdecd28000861
出典データセット
uspto-grants-2000_11
特許番号
US06143764

反応ノート

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