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

HRID 49185

Reaktionsgleichung

Reaktionsgleichung von HRID 49185
[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

A solution of 1-amino-5-(2-chlorophenyl)cyclohexen-3-one (2.7 g) in ethanol (50 ml) and toluene (150 m) was combined with acetyl acetoaldehyde dimethyl acetal (4.0 g) and 85% potassium hydroxide (0.67 g), and the mixture was heated under reflux. 85% Potassium hydroxide (0.14 g) was added three times at an interval of 30 minutes, and then heated under reflux further for 1 hour. The solvent was distilled off under reduced pressure, and the residue was combined with ethyl acetate, washed successively with water and saturated brine, and dried over magnesium sulfate. After concentrating under reduced pressure, the residue was subjected to a column chromatography on a silica gel (EtOAc-hexane) to obtain 7-(2-chlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (2.5 g) as a crystal. Melting point and NMR data were in agreement with those of the compound obtained in Reference Example 2.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperatureheated
  4. temperatureunder reflux further for 1 hour
  5. distillationThe solvent was distilled off under reduced pressure
  6. washwashed successively with water and saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationAfter concentrating under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-25a6346f6a0b46519b1f9908d027fc48
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706732B1

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