2-Hydroxy-5-methylbenzophenone → {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-(phenyl)methanone

HRID 228591

Reaktionsgleichung

Reaktionsgleichung von HRID 228591
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.[OH:16][C:17]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:16][C:17]1[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:18]=1[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20]

Komponenten

5

Edukt 2

HCID 738512-Hydroxy-5-methylbenzophenoneHCID 4596104-Chloro-6,7-dimethoxyquinoline

Produkt 1

HCID 24879061{2-[(6,7-Dimethoxy-4-quinolyl)oxy]-5-methylphenyl}-(phenyl)methanoneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinoline (58.6 mg), 2-hydroxy-5-methylbenzophenone (276 mg), and 4-dimethylaminopyridine (156 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160° C. for 5 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 the mixture was washed with a 1 N aqueous potassium hydroxide solution and saturated brine and was dried over anhydrous sodium 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 (98.9 mg, yield 95%).

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
  5. washthe mixture was washed with a 1 N aqueous potassium hydroxide solution and saturated brine
  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-e30471ad9dc540d0ab6ae9ecab3322aa
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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