Water → 2-Cyclohexyloxy-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochloride

HRID 1817817Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1817817
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Na].[Cl:9][C:10]1[CH:19]=[CH:18][C:17]2[C:16](=[O:20])[CH2:15][C:14]([CH3:22])([CH3:21])[CH2:13][C:12]=2[N:11]=1.O>C(OCC)C>[ClH:9].[CH:1]1([O:7][C:10]2[CH:19]=[CH:18][C:17]3[C:16](=[O:20])[CH2:15][C:14]([CH3:22])([CH3:21])[CH2:13][C:12]=3[N:11]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7966CyclohexanolHCID 5360545SodiumHCID 148125452-Chloro-7,7-dimethyl-7,8-dihydroquinolin-5(6H)-one

Produkt 1

HCID 690420072-Cyclohexyloxy-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one hydrochlorideAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of cyclohexanol (0.2 g, 2.0 mmol) in diethyl ether (10 ml) was added sodium (0.035 g, 1.5 mmol) and it was stirred at room temperature for 2.5 h. Then 2-chloro-7,7-dimethyl-7,8-dihydro-6H-quinolin-5-one (0.21 g, 1.0 mmol) was added and the resulting mixture was stirred at 30° C. for 24 h. Water (12 ml) was added and the mixture was extracted with ethyl acetate (2×10 ml). The organic phase was washed with water (10 ml) and dried over magnesium sulphate, then it was filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1) followed by treatment with a dry 0.5M HCl solution in diethyl ether to give the title compound (0.28 g, 47%) as a colorless solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at 30° C. for 24 h
  2. extractionthe mixture was extracted with ethyl acetate (2×10 ml)
  3. washThe organic phase was washed with water (10 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationit was filtered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel (petroleum ether-ethyl acetate, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-05014b9f1c45445d9de7fd56b50d8d96
Quelldatensatz
uspto-grants-2009_10
Patentnummer
US07598384B2

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