5-Bromo-2-hydroxybenzophenone → {5-Bromo-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-(phenyl)methanone

HRID 228590

Reaktionsgleichung

Reaktionsgleichung von HRID 228590
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.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([OH:31])=[C:21]([CH:30]=1)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([O:31][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)=[C:21]([C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:30]=1

Komponenten

5

Edukt 2

HCID 2290095-Bromo-2-hydroxybenzophenoneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Produkt 1

HCID 24879210{5-Bromo-2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-(phenyl)methanoneAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinoline (56.1 mg), 5-bromo-2-hydroxybenzophenone (361 mg), and 4-dimethylaminopyridine (168 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 7 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Chloroform was added to the residue, and mixture was washed with a 1 N aqueous potassium hydroxide solution and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform and by thin layer chromatography using acetone-hexane to give the title compound (110 mg, yield 94%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed
  3. distillationby distillation under the reduced pressure
  4. additionChloroform was added to the residue, and mixture
  5. washwas washed with a 1 N aqueous potassium hydroxide solution and saturated brine
  6. dry with materialwas dried over anhydrous magnesium 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-6f3beb0d05994b94832df27083e012ea
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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