(2-Nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine → (2-Aminophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

HRID 2358249Notes

Reaction equation

HRID 2358249 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][N:12]1[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]1=[O:20])([O-])=O>[Pd].O.CO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][N:12]1[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]1=[O:20]

Participants

5

Reactant 1

HCID 58911262(2-Nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

Product 1

HCID 58911264(2-Aminophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Palladium on charcoal (10% wt) was added to a solution of (2-nitrophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine a28 (1 eq, 2.747 g, 9.905 mmol) and NH4CO2H (5 eq, 49.9 mmol, 3.123 g) in water and methanol (1/1 (v/v), 35 ml). The resulting slurry was kept under agitation during 16 hours at room temperature, then filtration over celite and evaporation of the crude mixture gave (2-aminophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine a29 (2.232 g, 91%).

Workup

  1. filtrationfiltration
  2. customover celite and evaporation of the crude mixture

Sources & evidence

ORD record
ord-0e4000f112c9446689d7fe46f93e35af
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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