2,5-Dichloro-3-nitropyridine → 3-Amino-2,5-dichloropyridine

HRID 359642Notes

Reaction equation

HRID 359642 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1>O1CCOCC1.[Ni]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([Cl:11])[CH:6]=1

Participants

4

Reactant 1

HCID 80633312,5-Dichloro-3-nitropyridine

Product 1

HCID 27999993-Amino-2,5-dichloropyridineYield 75.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 129.2 g (0.69 mol) of 2,5-dichloro-3-nitropyridine in 1300 ml of dioxane is added 26.0 g of Raney-nickel, that has previously been washed with ethanol. This mixture is then hydrogenated with hydrogen under normal pressure at 20°-35° C. After uptake of 20% of the theoretical amount of hydrogen, another 30 g of washed Raney-nickel catalyst are added. After hydrogenating for 22 hours, the catalyst is filtered off, the solvent is evaporated and the residue is crystallized from hexane/ethyl acetate. Thus, 84.9 g of 3-amino-2,5-dichloropyridine (78% of the theory) are obtained, which melts at 129°-132° C.

Workup

  1. washhas previously been washed with ethanol
  2. customat 20°-35° C
  3. additionAfter uptake of 20% of the theoretical amount of hydrogen, another 30 g of washed Raney-nickel catalyst are added
  4. filtrationthe catalyst is filtered off
  5. customthe solvent is evaporated
  6. customthe residue is crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-f44a7d79fac84f0a96c74525e35e4f64
Source dataset
uspto-grants-1991_03
Patent number
US05002604

Reaction notes

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