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

HRID 2230987Notes

Reaction equation

HRID 2230987 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-dcbb4a137aac48a09f04cf63b7b3e976
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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