HCID 13647639, compound → HCID 13647649, compound

HRID 978701Notes

Reaction equation

HRID 978701 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([NH2:15])=[O:14])[C:8](=[O:16])[CH2:7]2)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([NH2:15])=[O:14])[C:8](=[O:16])[CH2:7]2

Participants

5

Reactant 2

HCID 13647639HCID 13647639, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13647649HCID 13647649, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5.0 g. of 5-nitro-2-oxindole-1-carboxamide in 110 ml. of N,N-dimethylformamide was added 0.5 g. of 10% palladium-on-carbon, and the resulting mixture was shaken under an atmosphere of hydrogen at an initial pressure of 5 kg/cm2 until hydrogen uptake ceased. The catalyst was removed by filtration, and the filtrate was diluted with brine and extracted with ethyl acetate. The extracts were dried (MgSO4) and evaporated in vacuo to give a dark-colored oil which solidified after trituration under water. This afforded 3.0 g. of the title compound as a yellow solid, mp 189°-191° C.

Workup

  1. customThe catalyst was removed by filtration
  2. additionthe filtrate was diluted with brine
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated in vacuo
  6. customto give a dark-colored oil which

Sources & evidence

ORD record
ord-88d6acb4386048548f9f05bc44ffd5ca
Source dataset
uspto-grants-1987_05
Patent number
US04665194

Reaction notes

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