4-Chloro-6,7-dimethoxyquinoline → (3-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone

HRID 1857208ノート

反応式

HRID 1857208 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[N:24]=[CH:23][CH:22]=1.CCCCCC.C(OCC)(=O)C>COCCOCCOC>[F:19][C:16]([F:17])([F:18])[C:12]1[CH:11]=[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][C:21]3[C:30]4[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[CH:3][CH:4]=2)=[O:9])[CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 21226206Ethyl acetate hexaneHCID 22132694(4-Hydroxyphenyl)[3-(trifluoromethyl)phenyl]methanone

生成物 1

HCID 22132736(3-Trifluoromethylphenyl){4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}methanone収率 28%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒

反応条件

温度
160 °C

実験手順

Under argon, 3-trifluoromethylphenyl 4-hydroxyphenyl ketone (432 mg) obtained in Example 139 and 4-chloro-6,7-dimethoxyquinoline (363 mg) were dissolved in diethylene glycol dimethyl ether (10 ml), and the solution was then refluxed at 160° C. for 11 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was 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 204 mg of the title compound (yield: 28%).

後処理

  1. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  2. dry with materialthe chloroform layer was dried with anhydrous magnesium sulfate
  3. customAfter removing the solvent
  4. distillationby reduced-pressure distillation
  5. 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-02de19f6a93443cebff46c1afe9f4751
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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