4-Chloropyridine → 4,4'-Bipyridine

HRID 2397602Notes

Reaction equation

HRID 2397602 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[Na+].C([O-])=O.[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Pd].O>[N:5]1[CH:6]=[CH:7][C:2]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)=[CH:3][CH:4]=1

Participants

7

Reactant 3

HCID 122884-ChloropyridineHCID 14798Sodium HydroxideHCID 2723810Sodium Formate2×

Product 1

HCID 111074,4'-BipyridineYield 46.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

4-Chloropyridine (11.35 parts), benzyltriethylammonium chloride (2.0 parts), sodium hydroxide liquor (32%; 13.5 parts), 3% palladium on charcoal (50% paste; 2.0 parts) and sodium formate (10.2 parts in water (30 parts) are stirred at the boil under reflux for 4 hours. Sodium formate (3.4 parts) is added and then the mixture held at the boil for a further 24 hours. The reaction mixture is cooled and then filtered. The residue is extracted continuously with hot methanol (100 parts) for 6 hours. The extract when evaporated to dryness gives 3.6 parts (46.2%) of 4,4'-bipyridyl.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. extractionThe residue is extracted continuously with hot methanol (100 parts) for 6 hours
  5. extractionThe extract when
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-a95c3f488ba547d983dc7504ad859980
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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