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

HRID 24463Notes

Reaction equation

HRID 24463 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 refluxed for 2 hours, concentrated to dryness and the residue taken up in ethyl acetate. The solids were removed by filtration and the filtrate washed twice with 1 N 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 1 N hydrochloric acid and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fd70c39b10b946298d6409a1a1303747
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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