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

HRID 1857208Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857208
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-02de19f6a93443cebff46c1afe9f4751
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143764

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