1-(3-Nitrophenyl)-1H-pyrrole-2,5-dione → 1-(3-Aminophenyl)-2,5-pyrrolidinedione

HRID 2086811Notes

Reaction equation

HRID 2086811 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH:13]=[CH:12][C:11]2=[O:16])[CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].O>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:11](=[O:16])[CH2:12][CH2:13][C:14]2=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 2367901-(3-Nitrophenyl)-1H-pyrrole-2,5-dione

Product 1

HCID 176078571-(3-Aminophenyl)-2,5-pyrrolidinedioneYield 55%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of N-(3-nitrophenyl)maleimide (26.3 g) in methanol-dioxane (1:1) was added suspension of palladium on carbon (2 g) in water. The reaction mixture was hydrogenated for 4 hours at 3 atm. (White crystal was precipitated.) The mixture was added 1N hydrochloric acid (ca. 300 ml) to dissolve the crude product. The mixture was filtrated and evaporated. Obtained residue was dissolved in water and basified by aqueous sodium hydrogencarbonate. Precipitate was collected by suction to give N-(3-aminophenyl)succinimide (12.6 g).

Workup

  1. customThe reaction mixture was hydrogenated for 4 hours at 3 atm. (White crystal was precipitated.) The mixture
  2. additionwas added 1N hydrochloric acid (ca. 300 ml)
  3. dissolutionto dissolve the crude product
  4. filtrationThe mixture was filtrated
  5. customevaporated
  6. dissolutionObtained residue was dissolved in water
  7. customPrecipitate was collected by suction

Sources & evidence

ORD record
ord-be67f824bc8548d0882ae297897c7bbb
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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