Ammonium formate → 3-(2-Oxo-2-pyrrolidin-1-ylethyl)aniline

HRID 546623Notes

Reaction equation

HRID 546623 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[O:12]=[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 576259941-[(3-Nitrophenyl)acetyl]pyrrolidine

Product 1

HCID 286896693-(2-Oxo-2-pyrrolidin-1-ylethyl)anilineYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2.12 g of 1-[(3-nitrophenyl)acetyl]pyrrolidine obtained in stage a) below in 50 mL of methanol are added, under argon, 4.56 g of ammonium formate and 96 mg of 10% palladium-on-charcoal. The reaction mixture is stirred at room temperature for 1 hour and then filtered through Celite and concentrated under reduced pressure. The residue is taken up in water and extracted with dichloromethane. The organic phase is then washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and concentrated under reduced pressure to give 1.46 g of 3-(2-oxo-2-pyrrolidin-1-ylethyl)aniline, the characteristics of which are as follows:

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated under reduced pressure
  3. extractionextracted with dichloromethane
  4. washThe organic phase is then washed with water and with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3c955372283c424da0c685d843bbbf40
Source dataset
uspto-grants-2011_05
Patent number
US07935819B2

Reaction notes

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