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

HRID 1369882Notes

Reaction equation

HRID 1369882 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 66.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron powder (5 g) was added in one portion to 9.8 g of 2′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL of glacial acetic acid was heated to 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 1N hydrochloric acid, water and then brine, dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on silica gel in ethyl acetate:hexane (1:2) to give 5.4 g 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 1N hydrochloric acid, water
  6. dry with materialbrine, dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel in ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-4116ab7ee9c3422fabfc8a221035e312
Source dataset
uspto-grants-2003_06
Patent number
US06579897B2

Reaction notes

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