2,4-Dichloro-3-nitro-6-(2-fluorophenyl)pyridine → 6-(2-Fluorophenyl)pyridin-3-amine

HRID 2380399Notes

Reaction equation

HRID 2380399 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-])=O)=[C:6](Cl)[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])[N:3]=1>CO.[Pd]>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[N:3][CH:2]=1

Participants

4

Reactant 1

HCID 189555872,4-Dichloro-3-nitro-6-(2-fluorophenyl)pyridine

Product 1

HCID 189555756-(2-Fluorophenyl)pyridin-3-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 2,4-dichloro-3 -nitro-6-(2-fluorophenyl)pyridine (1.6 g, 5.6 mmol) in methanol (100 ml) was added a catalytic amount of 10% palladium on carbon (100 mg). The mixture was hydrogenated at 50 psi for 8 hours then filtered through celite. The methanol was removed under reduced pressure and the residue was extracted with ethyl acetate from an aqueous solution saturated with potasssium carbonate. The extract was washed with brine, dried over sodium sulfate, filtered and concentrated to give 5-amino-2-(2-fluorophenyl)pyridine, which was used without further purification.

Workup

  1. filtrationthen filtered through celite
  2. customThe methanol was removed under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate from an aqueous solution saturated with potasssium carbonate
  4. washThe extract was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d6a4ffcff473467aa90dfde6a9ee9727
Source dataset
uspto-grants-1994_11
Patent number
US05367077

Reaction notes

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