2-Chloropyridine → 2,2'-Bipyridine

HRID 2397601Notes

Reaction equation

HRID 2397601 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])=O.[Na+].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[Pd].O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 79772-ChloropyridineHCID 14798Sodium HydroxideHCID 2723810Sodium Formate2×

Product 1

HCID 14742,2'-BipyridineYield 51.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

2-Chloropyridine (22.7 parts), benzyltriethylammonium chloride (8.0 parts), 3% palladium on charcoal (50% paste; 4.0 parts), sodium formate (20.4 parts) and sodium hydroxide liquor (32%; 27 parts) in water (60 parts) stirred at the boil under reflux for 4 hours. Sodium formate (6.8 parts) is then added tha the mixture held at the boil under reflux for a further 24 hours. The reaction mixture is cooled and then filtered. The residue is washed with ether (75 parts) and then the filtrate extracted with ether (2 × 70 parts). The combined ether extracts are dried over anhydrous magnesium sulphate. After removal of the drying agent the ether is distilled off. The residue is distilled under vacuum and the fraction b.pt. 150°-154° C./20 mm is collected giving 8.1 parts (51.9%) of 2,2'-bipyridyl.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureunder reflux for a further 24 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe residue is washed with ether (75 parts)
  6. extractionthe filtrate extracted with ether (2 × 70 parts)
  7. dry with materialThe combined ether extracts are dried over anhydrous magnesium sulphate
  8. customAfter removal of the drying agent the ether
  9. distillationis distilled off
  10. distillationThe residue is distilled under vacuum
  11. customthe fraction b.pt. 150°-154° C./20 mm is collected

Sources & evidence

ORD record
ord-c28ef6231b1e4baaaa1c015e3f75532b
Source dataset
uspto-grants-1977_05
Patent number
US04022795

Reaction notes

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