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

HRID 1937606Notes

Reaction equation

HRID 1937606 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 of glacial acetic acid and the mixture 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 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-a3c3bc3a5e0c49c89d8792b7f4a31812
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

Loading…