Butyn-2-one → 7-(2-Fluorophenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 1700515Notes

Reaction equation

HRID 1700515 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12](=[O:14])[CH2:11][C:10](=O)[CH2:9]1.[C:16]([O-])(=O)[CH3:17].[NH4+:20].[CH3:21][C:22](=O)[C:23]#C>C(O)CCCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:9][C:10]2[N:20]=[C:22]([CH3:23])[CH:21]=[C:16]([CH3:17])[C:11]=2[C:12](=[O:14])[CH2:13]1

Participants

5

Reactant 3

HCID 15018Butyn-2-one2×HCID 517165Ammonium AcetateHCID 136448415-(2-Fluorophenyl)cyclohexane-1,3-dione

Product 1

HCID 183176457-(2-Fluorophenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-oneYield 9.2%

Reagents, catalysts & solvents 1

HCID 62761-PentanolSolvent

Procedure

A mixture of 5-(2-fluorophenyl)cyclohexane-1,3-dione (1.0 g) and ammonium acetate (0.97 g) in 1-pentanol (30 ml) was refluxed for 30 minutes. To the mixture was added 3-butyn-2-one (0.97 g), and the mixture was refluxed for 14.5 hours. To the mixture was added 3-butyn-2-one (0.49 g), and the mixture was refluxed for 5 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated brine, dried with magnesium sulfate and concentrated under reduced pressure, and the residue was purified with silica gel column chromatography (EtOAc/hexane) to give oil of 7-(2-fluorophenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one (0.12 g).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperaturethe mixture was refluxed for 14.5 hours
  3. temperaturethe mixture was refluxed for 5 hours
  4. customUnder reduced pressure, the solvent was evaporated
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with water and saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe residue was purified with silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-dd9ce587efce4505818a057788cca13c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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