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

HRID 1762254Notes

Reaction equation

HRID 1762254 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[H][H]>O1CCOCC1.[Ni]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[C:5]([Cl:11])[CH:6]=1

Participants

5

Reactant 2

HCID 80633312,5-Dichloro-3-nitropyridineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 27999993-Amino-2,5-dichloropyridineYield 78%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

26.0 g of Raney nickel catalyst are washed with ethanol and then added to a solution of 129.2 g (0.69 mol) of 2,5-dichloro-3-nitropyridine in 1300 ml of dioxane. This mixture is hydrogenated with hydrogen under normal pressure and at a temperature in the range from 20° to 35° C. After reaction of 20% of the required amount of hydrogen, a further 30.0 g of Raney nickel catalyst are added to the reaction mixture. After a hydrogenation period of 22 hours, the catalyst is removed, the solvent is evaporated off and the residue is crystallised from ethyl acetate/hexane, affording 84.9 g (78% of theory) of 3-amino-2,5-dichloropyridine, m.p. 129°-132° C.

Workup

  1. wash26.0 g of Raney nickel catalyst are washed with ethanol
  2. customAfter a hydrogenation period of 22 hours, the catalyst is removed
  3. customthe solvent is evaporated off
  4. customthe residue is crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-39f6eb1685674e68be7fbc156854660c
Source dataset
uspto-grants-1989_05
Patent number
US04831148

Reaction notes

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