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4-Chloro-6,7-dimethoxyquinoline → Propyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-acetylbenzoate

HRID 228629
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228629
[C:1]([C:4]1[CH:15]=[C:8]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[C:7]([OH:16])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Cl[C:18]1[C:27]2[C:22](=[CH:23][C:24]([O:30][CH3:31])=[C:25]([O:28][CH3:29])[CH:26]=2)[N:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:29][O:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[O:30][CH3:31])[N:21]=[CH:20][CH:19]=[C:18]2[O:16][C:7]1[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:15][C:8]=1[C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078328Propyl 5-acetylsalicylate

Produkt 1

HCID 57756400Propyl 2-[(6,7-dimethoxy-4-quinolyl)oxy]-5-acetylbenzoateAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Propyl 5-acetylsalicylate (202 mg), 4-chloro-6,7-dimethoxyquinoline (101 mg), and 4-dimethylaminopyridine (164 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 120° C. overnight. The reaction solution was cooled to room temperature, and 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 water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure. The residue was purified by column chromatography using acetone-hexane to give the title compound (35 mg, yield 9%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-0e0c4e37f57f459d8ebd25c4fd2d5b6f
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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