Potassium Hydroxide → HCID 18317566, compound

HRID 1700487Notes

Reaction equation

HRID 1700487 reaction equation
[NH2:1][C:2]1[CH2:7][CH:6]([C:8]2[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:15])[CH2:5][C:4](=[O:16])[CH:3]=1.[OH-].[K+]>C(O)C.C1(C)C=CC=CC=1>[ClH:14].[Cl:14][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:15])[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 18317314HCID 18317314, compound

Product 1

HCID 18317566HCID 18317566, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

In a mixture of ethanol (23 ml) and toluene (70 ml) was dissolved 1-amino-5-(2,6-dichlorophenyl)cyclohexen-3-one (1.25 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (1.84 g) and granulated potassium hydroxide (303 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (62 mg), 30 minutes later; 1 hour later; and 1.5 hours, respectively. The reaction solution was stirred at the same temperature for 1 hour, cooled and concentrated under reduced pressure, and to the residue were added ethyl acetate (50 ml) and water (15 ml). The mixture was separated and the separated upper layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane, which was concentrated under reduced pressure. The residue was dissolved in a mixture of ether (4 ml) and ethanol (2 ml), and to the solution was added concentrated hydrochloric acid (0.25 ml). Precipitated crystals were filtered, washed with the same mixed solvent and dried to give 7-(2,6-dichlorophenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one hydrochloride (0.75 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. concentrationconcentrated under reduced pressure
  6. additionto the residue were added ethyl acetate (50 ml) and water (15 ml)
  7. customThe mixture was separated
  8. washthe separated upper layer was washed with saturated brine
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified with silica gel column chromatography (EtOAc/hexane)
  11. washeluted with ethyl acetate/hexane, which
  12. concentrationwas concentrated under reduced pressure
  13. dissolutionThe residue was dissolved in a mixture of ether (4 ml) and ethanol (2 ml)
  14. additionto the solution was added concentrated hydrochloric acid (0.25 ml)
  15. customPrecipitated crystals
  16. filtrationwere filtered
  17. washwashed with the same mixed solvent
  18. customdried

Sources & evidence

ORD record
ord-287c1578f6d84fad914c6157d61eefaf
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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