N,N-dimethyl-5-nitropyridin-2-amine → N2,N2-dimethylpyridine-2,5-diamine

HRID 1915684Notes

Reaction equation

HRID 1915684 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][N:4]=1>[Pd].C(O)C>[CH3:1][N:2]([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 75707N,N-dimethyl-5-nitropyridin-2-amine

Product 1

HCID 78642N2,N2-dimethylpyridine-2,5-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-(dimethylamino)-5-nitropyridine (1 eq) and 5% palladium on carbon (0.3 eq) in ethanol was stirred at room temperature and flushed with nitrogen. The reaction vessel was evacuated and purged with hydrogen three times. The reaction mixture was left under an atmosphere of hydrogen overnight. Nitrogen was flushed through the reaction and then the reaction was filtered through a celite pad. The celite pad was washed with excess ethanol before the solvent was removed by evaporation under reduced pressure to afford 2-(dimethylamino)-5-aminopyridine.

Workup

  1. customflushed with nitrogen
  2. customThe reaction vessel was evacuated
  3. custompurged with hydrogen three times
  4. customNitrogen was flushed through the reaction
  5. filtrationthe reaction was filtered through a celite pad
  6. washThe celite pad was washed with excess ethanol before the solvent
  7. customwas removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-81161a9fc7f04a2ba0945dc99f66d660
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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