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

HRID 1700479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1700479
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=2[CH3:15])[CH2:5][C:4](=[O:16])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[CH3:15][C:9]1[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:8]=1[CH:6]1[CH2:7][C:2]2[N:1]=[CH:7][CH:2]=[C:3]([CH3:4])[C:3]=2[C:4](=[O:16])[CH2:5]1

Komponenten

5

Edukt 2

HCID 14797Potassium Hydroxide2×HCID 183175811-Amino-5-(2,5-dimethylphenyl)cyclohexen-3-one

Produkt 1

HCID 183173177-(2,5-Dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneAusbeute 130,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
115 °C

Versuchsvorschrift

In a mixture of ethanol (35 ml) and toluene (90 ml) was dissolved 1-amino-5-(2,5-dimethylphenyl)cyclohexen-3-one (1.7 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.66 g) and granulated potassium hydroxide (440 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (90 mg), 30 minutes later; 1 hour later; and 1.5 hours, respectively. The reaction solution was stirred at the same temperature for 1 hour and cooled. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (40 ml) and water (20 ml). The mixture was shaken and separated ethyl acetate layer was washed with brine. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 7-(2,5-dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.37 g) as colorless crystals.

Aufarbeitung

  1. custom1 hour
  2. custom1.5 hours
  3. stirringThe reaction solution was stirred at the same temperature for 1 hour
  4. temperaturecooled
  5. customUnder reduced pressure, the solvent was evaporated
  6. additionto the residue were added ethyl acetate (40 ml) and water (20 ml)
  7. stirringThe mixture was shaken
  8. customseparated ethyl acetate layer
  9. washwas washed with brine
  10. customUnder reduced pressure, ethyl acetate was evaporated
  11. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)
  12. washeluted with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-8ba522bf3218489c807ae851a5a1a4bc
Quelldatensatz
uspto-grants-2002_02
Patentnummer
US06350749B1

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