4'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one

HRID 2121567Notes

Reaction equation

HRID 2121567 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[C:11]([N+:19]([O-])=O)[CH:10]=2)=[CH:5][CH:4]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:12]([CH2:15][C:16](=[O:17])[NH:19]3)=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 104935034'-Methoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 107286906-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-oneYield 45%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron powder (3.6 g) was added in one portion to 7.2 g of 4′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL of glacial acetic acid and heated at 100° C. overnight. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1N hydrochloric acid and brine, dried over anhydrous sodium sulfate and concentrated to give 2.7 g of 6-(4-methoxyphenyl)-2-oxindole as a rose colored solid.

Workup

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

Sources & evidence

ORD record
ord-4adb2a546f5e46d899a3242a7e568348
Source dataset
uspto-grants-2004_02
Patent number
US06696463B2

Reaction notes

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