O-Xylene → HCID 22132737, Verbindung

HRID 1857194Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1857194
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C1(C)C(C)=CC=CC=1.Cl[C:27]1[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:38][O:37][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][C:33]=1[O:39][CH3:40])[N:30]=[CH:29][CH:28]=[C:27]2[O:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 7237O-XyleneHCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 112298054-(4-hydroxybenzoyl)benzonitrile

Produkt 1

HCID 22132737HCID 22132737, VerbindungAusbeute 47,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

Under argon, 4-(4-hydroxybenzoyl)benzonitrile (230 mg) obtained in Example 123 and 4-dimethylaminopyridine (138 mg) were added to xylene (5 ml), and the admixture was stirred at room temperature for 1 hour. 4-Chloro-6,7-dimethoxyquinoline (230 mg) was added, and the admixture was refluxed with heat for 20 hours. The reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform, and the chloroform layer was then dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate and then by thin layer chromatography on silica gel eluting with chloroform/ethyl acetate (5/1) to obtain 199 mg of the title compound (yield: 47%).

Aufarbeitung

  1. temperaturethe admixture was refluxed
  2. temperaturewith heat for 20 hours
  3. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogen carbonate and chloroform
  4. dry with materialthe chloroform layer was then dried with anhydrous magnesium sulfate
  5. customAfter removing the solvent
  6. distillationby reduced-pressure distillation
  7. customthe resulting residue was purified by chromatography on silica gel eluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3caba43c70c54748946cdecd28000861
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06143764

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