Benzylamine → 2-Benzylamino-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride

HRID 1817820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817820
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[H-].[Na+]>C(#N)C.O.CS(C)=O>[ClH:1].[CH2:21]([NH:28][C:2]1[CH:11]=[CH:10][C:9]2[C:8](=[O:12])[CH2:7][C:6]([CH3:14])([CH3:13])[CH2:5][C:4]=2[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 4

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

Produkt 1

HCID 690384072-Benzylamino-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochlorideAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

2-Chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.315 g, 1.5 mmol) and potassium carbonate (0.83 g, 6 mmol) were added to a solution of benzylamine (0.2 g, 1.8 mmol) in dry acetonitrile (4 ml). The mixture was stirred at reflux for 48 h. DMSO (3 ml) and sodium hydride (0.05 g) were added and heating was continued for additional 5 h. Water (10 ml) was added and the mixture was extracted with chloroform (2×10 ml). The extract was dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (chloroform-methyl alcohol, 40:1), then treated by dry HCl in diethyl ether to give the title compound (0.1 g, 21%) as a colorless solid.

Aufarbeitung

  1. temperatureat reflux for 48 h
  2. temperatureheating
  3. extractionthe mixture was extracted with chloroform (2×10 ml)
  4. dry with materialThe extract was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (chloroform-methyl alcohol, 40:1)
  8. additiontreated by dry HCl in diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-a1777af844ac401cb7e3ca7d9dce4982
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598384B2

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