2,2-Dimethyl-N-(5-nitro-2-pyridinyl)propanamide → N-(5-Aminopyridin-2-yl)-2,2-dimethylpropanamide

HRID 1039102Notes

Reaction equation

HRID 1039102 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][N:7]=1)=[O:4]>CO.[Pd]>[NH2:12][C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([CH3:15])([CH3:1])[CH3:16])=[N:7][CH:8]=1

Participants

4

Reactant 1

HCID 32494522,2-Dimethyl-N-(5-nitro-2-pyridinyl)propanamide

Product 1

HCID 43144550N-(5-Aminopyridin-2-yl)-2,2-dimethylpropanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2,2-dimethyl-N-(5-nitropyridin-2-yl)propanamide (300 mg, 1.34 mmol) from Step 1 of this example was dissolved with stirring in MeOH (4.5 ml). Palladium on carbon (10%, 75 mg) was added and the slurry degassed, placed under an atmosphere of hydrogen (3×) and stirred at RT for 30 minutes. The mixture was filtered through CELITE, the filter cake washed with EtOAc (3×100 ml), the filtrates combined and the volatiles removed in vacuum to give the titled compound.

Workup

  1. customthe slurry degassed
  2. filtrationThe mixture was filtered through CELITE
  3. washthe filter cake washed with EtOAc (3×100 ml)
  4. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-cb04cae7361b4fd5835a09cfc36c758e
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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