Acetylacetone → 7-(5-Fluoro-2-methylphenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one

HRID 49208Notes

Reaction equation

HRID 49208 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:14])[CH2:11][C:10](=O)[CH2:9]2)[CH:7]=1.C([O-])(=O)C.[NH4+:21].[C:22]([CH2:25][C:26](=O)[CH3:27])(=O)[CH3:23]>C(O)CCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:16])=[C:6]([CH:8]2[CH2:9][C:10]3[N:21]=[C:22]([CH3:23])[CH:25]=[C:26]([CH3:27])[C:11]=3[C:12](=[O:14])[CH2:13]2)[CH:7]=1

Participants

5

Reactant 3

HCID 31261AcetylacetoneHCID 517165Ammonium AcetateHCID 183177715-(5-Fluoro-2-methylphenyl)cyclohexane-1,3-dione

Product 1

HCID 178239227-(5-Fluoro-2-methylphenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-oneYield 62.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 5-(5-fluoro-2-methylphenyl)-cyclohexane-1,3-dione (1.5 g) and ammonium acetate (1.6 g) in butanol(30 ml) was combined with acetylacetone (2.0 g) and heated under reflux for 3 days. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, washed successively with aqueous sodium hydrogen carbonate, water and saturated brine, and dried over magnesium sulfate. The mixture was concentrated under reduced pressure, and the residue was subjected to a column chromatography on a silica gel (ethyl acetate-hexane) to obtain 7-(5-fluoro-2-methylphenyl)-2,4-dimethyl-5,6,7,8-tetrahydroquinolin-5-one (1.2 g) as an oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 days
  3. distillationThe solvent was distilled off under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed successively with aqueous sodium hydrogen carbonate, water and saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5ba56389a6444e2d83fa92269cfceb15
Source dataset
uspto-grants-2004_03
Patent number
US06706732B1

Reaction notes

Loading…