Ammonium Acetate → 1-Amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one

HRID 1700699Notes

Reaction equation

HRID 1700699 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:8]2[CH2:13][C:12](=O)[CH2:11][C:10](=[O:15])[CH2:9]2)[CH:7]=1.C([O-])(=O)C.[NH4+:21]>C(O)C>[NH2:21][C:12]1[CH2:13][CH:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[CH3:16])[CH2:9][C:10](=[O:15])[CH:11]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 183177715-(5-Fluoro-2-methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 183175171-Amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(5-fluoro-2-methylphenyl)cyclohexane-1,3-dione (3.0 g) and ammonium acetate (3.1 g) in ethanol (50 ml) was refluxed for 14 hours. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in ethyl acetate. The mixture was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 1-amino-5-(5-fluoro-2-methylphenyl)cyclohexen-3-one, which was dissolved in ethanol (70 ml) and toluene (120 ml). To the mixture were added 3-oxobutylaldehydedimethylacetal (4.1 g) and powdery potassium hydroxide (0.57 g), and the mixture was refluxed. To the mixture was added powdery potassium hydroxide (0.14 g) 30 minutes later; powdery potassium hydroxide (0.14 g) and 3-oxobutylaldehydedimethylacetal (0.33 g) 1 hour later; and powdery potassium hydroxide (0.14 g) 1.5 hours later. Then, the mixture was stirred at the same temperature for 2 hours and cooled. Under reduced pressure, the solvent was evaporated, and to the residue was added ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, ethyl acetate was evaporated, and the residue was subjected to silica gel column (ethyl acetate-hexane) to give crystals, which were recrystallized from ethyl acetate-hexane to give 7-(5-fluoro-2-methylphenyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.5 g).

Workup

  1. customUnder reduced pressure, the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-6e733bcaa43e4b46841cd24f2f2a225b
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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