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

HRID 24325Notes

Reaction equation

HRID 24325 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 107556933'-Methoxy-3-nitrobiphenyl-4-acetic acid

Product 1

HCID 105860706-(3-Methoxyphenyl)-1,3-dihydroindol-2-oneYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3′-Methoxy-3-nitrobiphenyl-4-acetic acid (5.2 g) was dissolved in methanol and hydrogenated over 0.8 g of 10% palladium on carbon for 3 hours at room temperature. The catalyst was removed by filtration, washed with methanol and the filtrates combined and concentrated to give a brown solid. The solid was chromatographed on silica gel in ethyl acetate:hexane:acetic acid (33:66:1) to give 3.0 g of 6-(3-methoxypheny)-2-oxindole as a pink solid.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationconcentrated
  4. customto give a brown solid
  5. customThe solid was chromatographed on silica gel in ethyl acetate:hexane:acetic acid (33:66:1)

Sources & evidence

ORD record
ord-0ecbab625cfe4149ba4bfe1311e3a152
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Reaction notes

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