Xanthoxylin → 1-{4,6-Dimethoxy-2-[(6,7-dimethoxy-4-quinolyl)oxy]-phenyl}-1-ethanone

HRID 228548

Reaktionsgleichung

Reaktionsgleichung von HRID 228548
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:16][C:17]([C:19]1[C:24]([O:25][CH3:26])=[CH:23][C:22]([O:27][CH3:28])=[CH:21][C:20]=1[OH:29])=[O:18]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:28][O:27][C:22]1[CH:23]=[C:24]([O:25][CH3:26])[C:19]([C:17](=[O:18])[CH3:16])=[C:20]([O:29][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:21]=1

Komponenten

5

Edukt 2

HCID 66654XanthoxylinHCID 4596104-Chloro-6,7-dimethoxyquinoline

Produkt 1

HCID 577563651-{4,6-Dimethoxy-2-[(6,7-dimethoxy-4-quinolyl)oxy]-phenyl}-1-ethanoneAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinoline (56 mg), 2-hydroxy-4,6-dimethoxyacetophenone (196 mg), and 4-dimethylaminopyridine (122 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 residue, 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 (25 mg, yield 27%).

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 residue
  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-2698dd9263034d84b4c14d37e94e58bd
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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