3'-Ethoxy-3-nitrobiphenyl-4-acetic acid → 6-(3-Ethoxyphenyl)indolin-2-one

HRID 1243406Notes

Reaction equation

HRID 1243406 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17](O)=[O:18])=[C:12]([N+:20]([O-])=O)[CH:11]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]>C(O)(=O)C.[Fe]>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]3[C:13]([CH2:16][C:17](=[O:18])[NH:20]3)=[CH:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

4

Reactant 1

HCID 107806283'-Ethoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 106346366-(3-Ethoxyphenyl)indolin-2-oneYield 91%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Iron powder (2.4 g) was added in one portion to 4.6 g of 3′-ethoxy-3-nitrobiphenyl-4-acetic acid in 40 mL of glacial acetic acid and refluxed for 2 hours. The reaction mixture was concentrated to dryness, treated repeatedly with ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1N hydrochloric acid and brine and then dried over anhydrous sodium sulfate and concentrated to give 3.5 g (91% yield) of 6-(3-ethoxyphenyl)-2-oxindole as a light brown solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additiontreated repeatedly with ethyl acetate
  4. filtrationfiltered
  5. customto remove the insolubles
  6. washThe filtrate was washed twice with 1N hydrochloric acid and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7860318e115e4d70983df5716b16a3f3
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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