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

HRID 1728602Notes

Reaction equation

HRID 1728602 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.[H][H]>[Pd].C(O)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([N:2]([CH3:12])[CH3:1])=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 75707N,N-dimethyl-5-nitropyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 78642N2,N2-dimethylpyridine-2,5-diamineYield 49%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-Dimethylamino-5-nitropyridine (D34) (1.64 g, 9.8 mM) was stirred with 10% palladium on charcoal (0.16 g) in ethanol (200 ml) under 1 atmos. of hydrogen. After 6 h the catalyst was filtered off onto Kieselguhr and the filtrate was evaporated. The residue was dissolved in diethyl ether, filtered again, and chromatographed on silica gel (50 g) using ether as eluant. The eluted product was purified further by extraction with petrol (bp 60°-80° C.) to give the title compound as a reddish oil (0.66 g; 49%).

Workup

  1. filtrationAfter 6 h the catalyst was filtered off onto Kieselguhr
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in diethyl ether
  4. filtrationfiltered again
  5. customchromatographed on silica gel (50 g)
  6. customThe eluted product was purified further by extraction with petrol (bp 60°-80° C.)

Sources & evidence

ORD record
ord-242bc050e74d4d8588eaf1460877a04d
Source dataset
uspto-grants-1994_07
Patent number
US05328922

Reaction notes

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