1,2-Dichlorobenzene → N-Phenyl-5-chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]-benzamide

HRID 228637

Reaktionsgleichung

Reaktionsgleichung von HRID 228637
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[C:17]1[CH:32]=[CH:31][C:20]([NH:21][C:22](=[O:30])[C:23]2[C:24](=[CH:26][CH:27]=[CH:28][CH:29]=2)[OH:25])=[CH:19][CH:18]=1.[Cl:33]C1C=CC=CC=1Cl>CN(C)C1C=CN=CC=1>[C:20]1([NH:21][C:22](=[O:30])[C:23]2[CH:29]=[C:28]([Cl:33])[CH:27]=[CH:26][C:24]=2[O:25][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:31]=[CH:32][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 72391,2-DichlorobenzeneHCID 77253Benzamide, N-(4-chlorophenyl)-2-hydroxy-HCID 4596104-Chloro-6,7-dimethoxyquinoline

Produkt 1

HCID 57756427N-Phenyl-5-chloro-2-[(6,7-dimethoxy-4-quinolyl)oxy]-benzamideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 142844-(Dimethylamino)pyridineKatalysator

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

4-Chloro-6,7-dimethoxyquinoline (100 mg), 4′-chloro-salicylanilide (445 mg), and 4-dimethylaminopyridine (220 mg) were suspended in o-dichlorobenzene (1 ml), and the suspension was stirred at 140° C. for 4 hr. 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, and the residue was purified by column chromatography using acetone-hexane to give the title compound (38 mg, yield 20%).

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-74797ef604f641848eec90d7f66fdfbb
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

Verknüpfte Notizen

Wird geladen…