Pyridine → N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamide

HRID 486294Notes

Reaction equation

HRID 486294 reaction equation
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.FC(F)(F)C(O)=O.N1C=CC=CC=1.[CH:35]([C:38]1[CH:39]=[C:40]([N:44]([CH2:55][CH:56]([OH:59])[CH2:57][CH3:58])[C:45](=[O:54])[CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH:41]=[CH:42][CH:43]=1)([CH3:37])[CH3:36]>C(Cl)Cl.C(OCC)C>[CH:35]([C:38]1[CH:39]=[C:40]([N:44]([CH2:55][C:56](=[O:59])[CH2:57][CH3:58])[C:45](=[O:54])[CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([Cl:53])[CH:48]=2)[CH:41]=[CH:42][CH:43]=1)([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 2724130Cornforth reagentHCID 19097809N-(3-isopropylphenyl)-N-(2-hydroxybutyl)-3-chlorophenylacetic amide

Product 1

HCID 11783283N-(3-isopropylphenyl)-N-(2-oxobutyl)-3-chlorophenylacetamideYield 76.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

15.7 g (41.7 mmol) of pyridinium dichromate were dissolved in 80 ml of methylene chloride, and 1.4 ml of trifluoroacetic acid and 0.9 ml of pyridine were added thereto. Next, 10 ml of a methylene chloride solution containing 10.0 g (27.8 mmol) of N-(3-isopropylphenyl)-N-(2-hydroxybutyl)-3-chlorophenylacetic amide obtained in Example 1 were added dropwise to the solution, while refluxed and stirred. Reaction was then carried out at the same temperature for 4 hours, and the resultant reaction mixture was then poured into 200 ml of diethyl ether. Insolubles were removed by filtration and the solvent was distilled off under reduced pressure, and the solution was then purified through silica gel column chromatography (an eluent: hexane/ethyl acetate=7/3) to obtain 7.61 g of the desired product in an oily state (yield: 76.2%).

Workup

  1. additionwere added dropwise to the solution
  2. temperaturewhile refluxed
  3. customReaction
  4. customthe resultant reaction mixture
  5. customInsolubles were removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe solution was then purified through silica gel column chromatography (an eluent

Sources & evidence

ORD record
ord-694031128d4c40bc8c4d6b3cddf45311
Source dataset
uspto-grants-1994_03
Patent number
US05290949

Reaction notes

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