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4-Chloro-6,7-dimethoxyquinoline → 4-(5,6-Dimethyl-2-phenyl-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228810
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228810
[CH3:1][C:2]1[CH:3]=[C:4]([OH:15])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:7]=1[CH3:8].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][CH:18]=1>CN(C1C=CN=CC=1)C.ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[CH:3]=[C:4]([O:15][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][CH:18]=2)[C:5]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:6][C:7]=1[CH3:8]
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Komponenten

5

Edukt 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 230783805,6-Dimethyl-2-phenyl-pyridin-3-ol

Produkt 1

HCID 230785864-(5,6-Dimethyl-2-phenyl-pyridin-3-yloxy)-6,7-dimethoxy-quinolineAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 72391,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

1,2-Dichlorobenzene (4.5 ml) was added to 5,6-dimethyl-2-phenyl-pyridin-3-ol (267 mg), 4-chloro-6,7-dimethoxyquinoline (100 mg), and 4-(N,N-dimethylamino)pyridine (164 mg), and the mixture was stirred at 140° C. for 8 hr. The reaction solution was cooled to room temperature, and the solvent was then removed by distillation under the reduced pressure. Water was 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 by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using hexane-acetone to give the title compound (159 mg, yield 92%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled to room temperature
  2. customthe solvent was then removed by distillation under the reduced pressure
  3. additionWater was 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 by distillation under the reduced pressure
  8. customthe residue was purified by thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f27b737fd7d84b73ab261a8331b9196a
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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