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

HRID 1790982Notes

Reaction equation

HRID 1790982 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 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 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 1 N hydrochloric acid and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-72684266cfd64a47babebee184279430
Source dataset
uspto-grants-2006_07
Patent number
US07071332B2

Reaction notes

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