Methanol → 6-(3-Methoxyphenyl)-1,3-dihydroindol-2-one

HRID 1243466Notes

Reaction equation

HRID 1243466 reaction equation
FC(F)(F)C1C=CC(NS([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16]3)(=O)=O)=CC=1.[CH3:25][OH:26]>[Pd]>[CH3:25][O:26][C:13]1[CH:21]=[C:20]([C:21]2[CH:20]=[C:19]3[C:15]([CH2:16][C:17](=[O:22])[NH:18]3)=[CH:14][CH:13]=2)[CH:19]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 97987775-(4-Trifluoromethylphenylaminosulfonyl)-2-oxindole

Product 1

HCID 105860706-(3-Methoxyphenyl)-1,3-dihydroindol-2-oneYield 75%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

3′-Methoxy-3-nitrobiphenyl-4-acetic acid (5:2 g) was dissolved in methanol and hydrogenated over 0.8 g 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 (75% yield based on 4-fluoro-3′-methoxy-3-nitrobiphenyl) 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-f00e1ababf5f42059b23cb42262ef9d1
Source dataset
uspto-grants-2006_10
Patent number
US07119090B2

Reaction notes

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