Potassium Carbonate → 1-{3-[7-(3-Hydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone

HRID 229081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 229081
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([C:23](=[O:25])[CH3:24])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:26][CH3:27].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][OH:38]>CN(C)C=O>[OH:38][CH2:37][CH2:36][CH2:35][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([C:23](=[O:25])[CH3:24])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:26][CH3:27]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 136131623HCID 136131623, Verbindung2×

Produkt 1

HCID 577564041-{3-[7-(3-Hydroxy-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanoneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1-[3-(7-Hydroxy-6-methoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone (compound 390) (50 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (58 mg) and 3-bromo-1-propanol (0.03 ml) were added to the solution, and the mixture was stirred at room temperature overnight. 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 saturated brine 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 chloroform-acetone to give the title compound (44 mg, yield 74%).

Aufarbeitung

  1. customto prepare a solution
  2. customThe solvent was removed by distillation under the reduced pressure, water
  3. additionwas then added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe chloroform layer was washed with saturated brine
  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-41b7844bc15e43ffb19ba6c276d29819
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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