Water → HCID 23078469, Verbindung

HRID 228742

Reaktionsgleichung

Reaktionsgleichung von HRID 228742
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[N:19][CH:20]=[C:21]([OH:23])[CH:22]=1.O>CN(C)C1C=CN=CC=1.ClC1C=CC=CC=1Cl>[Cl:16][C:17]1[CH:22]=[C:21]([O:23][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:20]=[N:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 5823053-Hydroxy-5-chloropyridine

Produkt 1

HCID 23078469HCID 23078469, VerbindungAusbeute 81,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinoline (245 mg), 3-chloro-5-pyridinol (277 mg), and 4-dimethylaminopyridine (377 mg) were suspended in o-dichlorobenzene (13 ml), and the mixture was stirred at 140° C. for 6 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous sodium hydroxide solution and 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 (283 mg, yield 81%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a71a8a9bce59413cbea550df5d082d41
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

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