3-Nitro-biphenyl-4-acetic acid → 6-Phenyl-1,3-dihydro-indol-2-one

HRID 2121419Notes

Reaction equation

HRID 2121419 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:8][C:9]=1[CH2:10][C:11](O)=[O:12])([O-])=O>C(O)(=O)C.[Fe]>[C:14]1([C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][C:11](=[O:12])[NH:1]3)=[CH:8][CH:7]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 104913603-Nitro-biphenyl-4-acetic acid

Product 1

HCID 105363846-Phenyl-1,3-dihydro-indol-2-oneYield 93%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (2.6 g) was added all at once to 4.5 g of 3-nitrobiphenyl-4-acetic acid in 40 mL of acetic acid. The mixture was refluxed for 2 hours, concentrated to dryness and taken up in ethyl acetate. The solids were removed by filtration and the filtrate washed twice with 1N hydrochloric acid and brine and dried over anhydrous sodium sulfate. The filtrate was concentrated to give 3.4 g (93% yield) of 6-phenyl-2-oxindole as a light brown solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated to dryness
  3. customThe solids were removed by filtration
  4. washthe filtrate washed twice with 1N hydrochloric acid and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e9ff6d8f34e34035a21bc50ee1164ec1
Source dataset
uspto-grants-2004_02
Patent number
US06696448B2

Reaction notes

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