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Water → 4-(2-Cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinoline

HRID 228738
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228738
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[C:17]([OH:22])=[N:18][CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[CH:29]1(Br)[CH2:33][CH2:32][CH2:31][CH2:30]1.O>C(Cl)(Cl)Cl>[CH:29]1([O:22][C:17]2[C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178486809HCID 178486809, Verbindung

Produkt 1

HCID 230783854-(2-Cyclopentyloxy-pyridin-3-yloxy)-6,7-dimethoxy-quinolineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212
Chloroform
Lösungsmittel

Versuchsvorschrift

6,7-Dimethoxy-4-(2-hydroxy-pyridin-3-yloxy)-quinoline (21 mg) was dissolved in chloroform (7 ml) to prepare a solution. Potassium carbonate (300 mg) and cyclopentyl bromide (0.2 ml) were added to the solution. The mixture was stirred at room temperature overnight, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic 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 column chromatography using acetone-chloroform to give the title compound (14 mg, yield 55%).

Aufarbeitung

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e73a2fae1fa34805996adcfee01b8cde
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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