Phenylhydrazine → HCID 54163397, compound

HRID 1646755Notes

Reaction equation

HRID 1646755 reaction equation
O=[C:2]([CH2:7][CH2:8][CH:9]=[CH2:10])[C:3]([O:5][CH3:6])=[O:4].[C:11]1([NH:17]N)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:6][O:5][C:3]([C:2]1[NH:17][C:11]2[C:16]([C:7]=1[CH2:8][CH:9]=[CH2:10])=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:4]

Participants

5

Reactant 2

HCID 7516PhenylhydrazineHCID 15552591Methyl 2-oxohex-5-enoate

Product 1

HCID 54163397HCID 54163397, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 241BenzeneSolvent

Procedure

The solution of methyl 2-oxo-5-hexenoate (19.5 g), phenylhydrazine (14.8 g) and anhydrous p-toluenesulfonic acid (0.5 g) in dry benzene was refluxed for 0.5 hour. The solution of anhydrous p-toluenesulfonic acid (35.3 g) in dry-benzene (150 ml) was added to the solution at 50° C. over five minutes. After being stirred at 50°-60° C. for 1 hour, the mixture was refluxed for 2 hours. After cooling, the reaction mixture was diluted with chilled water and extracted twice with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (10% ethyl acetate-toluene) to give 3-allyl-2-indolecarboxylic acid methyl ester (13.6 g) as crystals.

Workup

  1. dry with materialThe solution of anhydrous p-toluenesulfonic acid (35.3 g) in dry-benzene (150 ml)
  2. additionwas added to the solution at 50° C. over five minutes
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureAfter cooling
  5. additionthe reaction mixture was diluted with chilled water
  6. extractionextracted twice with ethyl acetate
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by silica gel column chromatography (10% ethyl acetate-toluene)

Sources & evidence

ORD record
ord-a87cf499337e45ddb76e879f37214667
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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