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

HRID 49126Notes

Reaction equation

HRID 49126 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 chips (2.6 g) were added all at once to 4.5 g of 3-nitrobiphenyl-4-acetic acid in 40 mL of acetic acid. The mixture was heated to reflux for 2 hours, concentrated to dryness and taken up in ethyl acetate. The solids were removed by filtration and the filtrate was 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 heated
  2. temperatureto reflux for 2 hours
  3. concentrationconcentrated to dryness
  4. customThe solids were removed by filtration
  5. washthe filtrate was washed twice with 1N hydrochloric acid and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d27c432970db48f6aa761702e7d002d4
Source dataset
uspto-grants-2004_03
Patent number
US06706709B2

Reaction notes

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