Sodium Acetate → 3-(4-Pyridyl)aniline

HRID 484779Notes

Reaction equation

HRID 484779 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)=[CH:4][C:3]=1[N+:14]([O-])=O.C([O-])(=O)C.[Na+].[H][H]>[Pd].C(O)(=O)C>[NH2:14][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][CH:2]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 135033054-(4-Chloro-3-nitrophenyl)pyridineHCID 178418361HCID 178418361, compound

Product 1

HCID 4595233-(4-Pyridyl)anilineYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A Paar shaker bottle was charged with 0.2 g (0.85 mmol) of 4-(4-chloro-3-nitrophenyl)pyridine, 0.07 g (0.85 mmol) of sodium acetate, 0.02 g of 5% palladium-on-carbon, and 3 ml of glacial acetic acid. It was then charged with hydrogen to 40 psi, and the shaker was turned on. The reaction mixture was heated to 60°-70° C. and maintained at that temperature for two hours, after which the reaction was stopped and the catalyst removed by filtration. To the filtrate was added water and then 50% aqueous caustic to a pH greater than 7. The reaction mixture was extracted with methylene chloride. The methylene chloride fraction was washed, dried, and evaporated. Analysis of the reaction mixture showed that the process resulted in an 83% yield of 4-(3-aminophenyl)pyridine.

Workup

  1. temperatureThe reaction mixture was heated to 60°-70° C.
  2. temperaturemaintained at that temperature for two hours
  3. customthe catalyst removed by filtration
  4. additionTo the filtrate was added water
  5. extractionThe reaction mixture was extracted with methylene chloride
  6. washThe methylene chloride fraction was washed
  7. customdried
  8. customevaporated

Sources & evidence

ORD record
ord-b63d686facdf47a0a14c0b35c2c03533
Source dataset
uspto-grants-1985_08
Patent number
US04533735

Reaction notes

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