5-Nitro-2-oxindole → 5-Amino-2-oxindole

HRID 2191456Notes

Reaction equation

HRID 2191456 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7]2

Participants

4

Reactant 1

HCID 2303665-Nitro-2-oxindole

Product 1

HCID 27732135-Amino-2-oxindoleYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5-Nitro-1,3-dihydro-indol-2-one 30b (3.56 g, 20 mmol) was dissolved in 200 ml of acetic acid under stirring, and added with palladium on activated carbon (1.0 g, 5%) to the solution at room temperature. The reaction mixture was stirred under a hydrogen atmosphere. After thin lay chromatography showed the disappearance of starting materials, the reaction mixture was filtered, and concentrated under reduced pressure to obtain the title compound 5-amino-1,3-dihydro-indol-2-one 30c (2.04 g, yield 68.9%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred under a hydrogen atmosphere
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf951429bfee4245aa30c284b5c328f0
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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