2'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(2-Methoxyphenyl)-1,3-dihydroindol-2-one

HRID 1815424Notes

Reaction equation

HRID 1815424 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[C:11]([N+:19]([O-])=O)[CH:10]=1>C(O)(=O)C.[Fe]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:10]=[C:11]2[C:12]([CH2:15][C:16](=[O:17])[NH:19]2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 107796192'-Methoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 105619756-(2-Methoxyphenyl)-1,3-dihydroindol-2-oneYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron chips (5 g) were added in one portion to 9.8 g 2′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL glacial acetic acid and the mixture was heated at 100° C. for 3 hours. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1 N hydrochloric acid, water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel using ethyl acetate:hexane 1:2 to give 5.4 g (69% yield based on 5-bromo-2-fluoronitrobenzene) of 6-(2-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 1 N hydrochloric acid, water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-861a123974854a649b90dfe4ed0440f4
Source dataset
uspto-grants-2005_04
Patent number
US06878733B1

Reaction notes

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