5-Chloro-2-fluoro-3-nitropyridine → 5-Chloro-2-fluoropyridin-3-amine

HRID 1762265Notes

Reaction equation

HRID 1762265 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[C:5]([F:8])=[N:6][CH:7]=1.[H][H]>C(O)C.[Ni]>[NH2:9][C:4]1[C:5]([F:8])=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 2

HCID 122757685-Chloro-2-fluoro-3-nitropyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 200428885-Chloro-2-fluoropyridin-3-amineYield 76.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

7.5 g (0.042 mol) of 5-chloro-2-fluoro-3-nitropyridine are dissolved in 80 ml of ethanol. This solution is hydrogenated with hydrogen, in the presence of 1 g of Raney nickel catalyst, under normal pressure and at a temperature in the range from 20° to 25° C. After a hydrogenation period of 20 hours, the catalyst is removed and the solvent is evaporated off. The residue is taken up in ethyl acetate and the resultant solution is filtered through a layer of silica gel. The solvent is evaporated off and the residue is triturated in hexane. The precipitate is subsequently filtered and dried, affording 4.7 g (76%) of 3-amino-5-chloro-2-fluoropyridine, m.p. 74° C.

Workup

  1. customAfter a hydrogenation period of 20 hours, the catalyst is removed
  2. customthe solvent is evaporated off
  3. filtrationthe resultant solution is filtered through a layer of silica gel
  4. customThe solvent is evaporated off
  5. customthe residue is triturated in hexane
  6. filtrationThe precipitate is subsequently filtered
  7. customdried

Sources & evidence

ORD record
ord-2e2791366d20469bbd666d7609e23186
Source dataset
uspto-grants-1989_05
Patent number
US04831148

Reaction notes

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