1-{[(3-Nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one → 1-{[(3-Aminopyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one

HRID 1926756Notes

Reaction equation

HRID 1926756 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].O.CO>[NH2:1][C:4]1[C:5]([NH:10][CH2:11][N:12]2[CH2:16][CH:15]([CH2:17][CH2:18][CH3:19])[CH2:14][C:13]2=[O:20])=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 577430171-{[(3-Nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one

Product 1

HCID 577430941-{[(3-Aminopyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-oneYield 113.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Palladium on charcoal (10% wt, 0.478 g) is added to a solution of 1-{[(3-nitropyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one x77 (1 eq, 2.5 g, 8.983 mmol) and NH4CO2H (5 eq, 44.9 mmol, 2.832 g) in water and methanol (1/1 (v/v), 35 ml). The resulting slurry is kept under agitation during 16 hours at room temperature, then filtration over celite and evaporation of the crude mixture afford 2.524 g of 1-{[(3-aminopyridin-2-yl)amino]methyl}-4-propylpyrrolidin-2-one x78.

Workup

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

Sources & evidence

ORD record
ord-5a0176395d24461c91cddee8372e3893
Source dataset
uspto-grants-2012_05
Patent number
US08183241B2

Reaction notes

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