1-(3-nitrophenyl)pyrrolidin-2-one → 1-(3-Aminophenyl)pyrrolidin-2-one

HRID 2086069Notes

Reaction equation

HRID 2086069 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[CH2:14][CH2:13][CH2:12][C:11]2=[O:15])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 15128701-(3-nitrophenyl)pyrrolidin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 6839561-(3-Aminophenyl)pyrrolidin-2-oneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-(3-nitrophenyl)pyrrolidin-2-one (3.0 g, 15 mmol) in ethanol (50 ml) was heated until complete solution was obtained. The solution was cooled to ambient temperature then treated with 10% palladium on charcoal (150 mg) and hydrogenated at 50 psi until hydrogen uptake ceased (ca. 2 hours). The mixture was filtered through a glass microfibre filter paper (Whatman GF/A) and evaporated to dryness to give 1-(3-aminophenyl)pyrrolidin-2-one as a pale green oil (2.6 g, 100%) which was used without purification.

Workup

  1. temperaturewas heated until complete solution
  2. customwas obtained
  3. custom(ca. 2 hours)
  4. filtrationThe mixture was filtered through a glass microfibre
  5. filtrationfilter paper (Whatman GF/A)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-413d825ca72a4efc985dce8771bdc787
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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