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

HRID 1860860Notes

Reaction equation

HRID 1860860 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 chips (2.4 g) were added in one portion to 4.6 g of 3′-ethoxy-3-nitrobiphenyl-4-acetic acid in glacial acetic acid (40 ml). The mixture was refluxed for 2 hours. The reaction mixture was cooled and concentrated to dryness. The residue was treated repeatedly with ethyl acetate and filtered to remove insolubles. The filtrate was washed twice with 1 N hydrochloric acid and brine, dried over anhydrous sodium sulfate and concentrated to give 3.5 g (91%) of 6-(3-ethoxyphenyl)-2-oxindole as a light brown solid.

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated to dryness
  4. additionThe residue was treated repeatedly with ethyl acetate
  5. filtrationfiltered
  6. customto remove insolubles
  7. washThe filtrate was washed twice with 1 N hydrochloric acid and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-efbebdce83324cb3a7230ea28ac6a21e
Source dataset
uspto-grants-2003_03
Patent number
US06531502B1

Reaction notes

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