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4-Chloro-6,7-dimethoxyquinoline → Methyl 8-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-phenyl]-8-oxo-octanoate

HRID 228719
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228719
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].Cl[C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[CH3:33][O:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][C:28]=1[O:34][CH3:35])[N:25]=[CH:24][CH:23]=[C:22]2[O:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9](=[O:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 23078392Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate

Produkt 1

HCID 23078555Methyl 8-[2-(6,7-dimethoxy-quinolin-4-yloxy)-5-methyl-phenyl]-8-oxo-octanoateAusbeute 3,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysator
HCID 7239
1,2-Dichlorobenzene
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Methyl 8-(2-hydroxy-5-methyl-phenyl)-8-oxo-octanoate (271 mg), 4-chloro-6,7-dimethoxyquinoline (220 mg), and 4-dimethylaminopyridine (237 mg) were suspended in o-dichlorobenzene (20 ml) to prepare a suspension which was then 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 by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give the title compound (16 mg, yield 3.5%).

Aufarbeitung

  1. customto prepare a suspension which
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was removed by distillation under the reduced pressure
  4. additionWater was then added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ba3c43e315f4bf9a1b448b5cece57f5
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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