Potassium Hydroxide → 7-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700483Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700483
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[CH2:5][C:4](=[O:15])[CH:3]=1.CO[CH:18](OC)[CH2:19][C:20](=O)[CH3:21].[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:18][CH:19]=[C:20]([CH3:21])[C:3]=2[C:4](=[O:15])[CH2:5]1

Komponenten

6

Edukt 3

HCID 14797Potassium Hydroxide2×HCID 2285484,4-Dimethoxy-2-butanoneHCID 98593161-Amino-5-(2-chlorophenyl)cyclohexen-3-one

Produkt 1

HCID 110655617-(2-Chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneAusbeute 75,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.7 g) in ethanol (50 ml) and toluene (150 ml) were added acetylacetoaldehyde-dimethylacetal (4.0 g) and 85% potassium hydroxide (0.67 g), and the mixture was refluxed. With intervals of 30 minutes, 85% potassium hydroxide (0.14 g) was added 3 times to the mixture. Then, the mixture was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The mixture was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was subjected to silica gel column chromatography (EtOAc/hexane) to give crystals of 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (2.5 g).

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperatureThen, the mixture was refluxed for 1 hour
  3. customUnder reduced pressure, the solvent was evaporated
  4. additionto the residue was added ethyl acetate
  5. washThe mixture was washed with water and saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationUnder reduced pressure, the mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-831e1529f6c34b629c15543086ac9d64
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

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