6-Iodo-2-nitrophenyl acetic acid → 1-Hydroxy-4-iodo-1,3-dihydro-indol-2-one

HRID 2191521Notes

Reaction equation

HRID 2191521 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=[O:9])[C:3]=1[CH2:11][C:12]([OH:14])=O>C(O)C.[Pd]>[OH:9][N:8]1[C:4]2[C:3](=[C:2]([I:1])[CH:7]=[CH:6][CH:5]=2)[CH2:11][C:12]1=[O:14]

Participants

4

Reactant 1

HCID 147409746-Iodo-2-nitrophenyl acetic acid

Product 1

HCID 147409771-Hydroxy-4-iodo-1,3-dihydro-indol-2-oneYield 63.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2-Iodo-6-nitro-phenyl)-acetic acid 74d (0.91 g, 3 mmol) was dissolved in ethanol (30 ml, 95%), and added with palladium on activated carbon (30 mg, 3%) to the solution. Upon completion of the addition, the reaction mixture was stirred for 2 hours under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 1-hydroxy-4-iodo-1,3-dihydro-indol-2-one 74e (516 mg, yield 63.4%) as a white solid.

Workup

  1. additionUpon completion of the addition
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-63b592e1b37e433dbc966d7e611a0d51
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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