4-Chloropyridine → 4,4'-Bipyridine

Participants

Reaction Steps

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.

Provenance & Evidence