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

HRID 1700479Notes

Reaction equation

HRID 1700479 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

HCID 183173177-(2,5-Dimethylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-oneYield 130.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8ba522bf3218489c807ae851a5a1a4bc
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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