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

HRID 1815411Notes

Reaction equation

HRID 1815411 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 3′-ethoxy-3-nitrobiphenyl-4-acetic acid in 40 mL glacial acetic acid and the mixture refluxed for 2 hours. The reaction mixture was concentrated to dryness, treated repeatedly with ethyl acetate and filtered to remove insoluble material. The filtrate was washed twice with 1 N hydrochloric acid then with brine, 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. temperaturethe mixture refluxed for 2 hours
  2. concentrationThe reaction mixture was concentrated to dryness
  3. additiontreated repeatedly with ethyl acetate
  4. filtrationfiltered
  5. customto remove insoluble material
  6. washThe filtrate was washed twice with 1 N hydrochloric acid
  7. dry with materialwith brine, dried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d12ed63097444f26ae8b2d619fd28414
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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