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

HRID 1243396Notes

Reaction equation

HRID 1243396 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-9c87de484040402c9ea2acb80a8d4e43
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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