4-Chloro-6,7-dimethoxyquinoline → Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(2,4-difluorophenyl)benzoate

HRID 228620

Reaktionsgleichung

Reaktionsgleichung von HRID 228620
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:19]=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:12]([OH:20])=[CH:11][CH:10]=1.Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][CH:23]=[C:22]2[O:20][C:12]1[CH:11]=[CH:10][C:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])=[CH:19][C:13]=1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Komponenten

5

Edukt 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078331Ethyl 2',4'-Difluoro-4-hydroxy[1,1'-biphenyl]-3-carboxylate

Produkt 1

HCID 57756448Ethyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-(2,4-difluorophenyl)benzoateAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 72391,2-DichlorobenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Ethyl 5-(2,4-difluorophenyl)salicylate (188 mg), 4-chloro-6,7-dimethoxyquinoline (57 mg), and 4-dimethylaminopyridine (93 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (13 mg, yield 24%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was removed by distillation under the reduced pressure
  3. additionWater was then added to the reaction solution
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with water
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customThe solvent was removed
  8. distillationby distillation under the reduced pressure
  9. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5b1485f1413d4bbda7b3af624a1e565c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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