Potassium Carbonate → N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamide

HRID 1291608

Reaktionsgleichung

Reaktionsgleichung von HRID 1291608
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:17]([NH:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O.O>[C:17]([NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:30]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[O:31])=[CH:33][CH:34]=1)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 694601,2,3,4-TetrahydroquinolineHCID 125009584-Benzoylaminobenzoyl chloride

Produkt 1

HCID 10642000N-[4-(3,4-dihydroquinolin-1(2H)-ylcarbonyl)phenyl]benzamideAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2,3,4-tetrahydroquinoline (28.7 g) in acetone (400 ml) and water (200 ml) is added potassium carbonate (38.8 g) and further thereto is added 4-benzoylaminobenzoyl chloride (56 g) under ice-cooling. The mixture is stirred at room temperature overnight. Water is added to the reaction mixture, and the mixture is extracted with dichloromethane. The extract is dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The resulting residue is purified by silica gel column chromatography and recrystallized from methanol to give 1-[4-(benzoylamino)benzoyl]-1,2,3,4-tetrahydroquinoline (57 g) as white powder, m.p. 202.5°-203.5° C.

Aufarbeitung

  1. temperaturecooling
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography
  6. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-eb3bd6cc2e06472a8f61b505918f3244
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05753677

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