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

HRID 18123

Reaction equation

HRID 18123 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>CC(N(C)C)=O.[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 50.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 h. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

Workup

  1. customfor 16 h
  2. customThe catalyst was removed by filtration
  3. additionthe filtrate was diluted with ether (2 L)

Sources & evidence

ORD record
ord-c74a7df036034b16a9d90a9fbaa46b63
Source dataset
uspto-grants-2010_06
Patent number
US07741336B2

Linked notes

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