2,2'-Bipyridine → HCID 58965485, compound

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Reaction Steps

2,2'-Bipyridine, 4,4'-dicarboxylic acid (1.0 g, 4.1 mol) is refluxed in 10 mL of thionyl chloride for 5 hours. The thionyl chloride is removed under reduced pressure, and added to 100 mL of toluene. The mixture is brought to a boil and filtered (gravity) into a cold stirring solution containing diethylamine (600 mg, 8.2 mmol), triethylamine (836 mg, 8.3 mmol) and 50 mL of toluene. The resulting solution is allowed to stir at room temperature for 30 minutes. The solution is poured into 100 mL of saturated sodium carbonate solution, and the layers are separated. The aqueous phase is extracted twice with 50 mL portions of chloroform. The extracts are combined with the toluene, and the volume reduced to about 10 mL by distillation. Heptane (50 ml) is added to the residue, and the resulting solid is filtered giving 2,2'-bipyridine-4,4'-dicarboxylic acid, N,N diethyl amide, as a low melting solid (500 mg).

Provenance & Evidence