Description
2,2''-Bipyridine-5,5''-dicarboxylic acid is a heterocyclic building block. It has been used in the synthesis of metal-organic frameworks for water oxidation, organic photocatalysis, and carbon dioxide reduction.
Synthesis
The general procedure for the synthesis of 2,2'-bipyridine-5,5'-dicarboxylic acid from 5,5'-dimethyl-2,2'-bipyridine was carried out as follows: 5,5'-dimethyl-2,2'-bipyridine (1.0 g) was dissolved in water (35 ml) and potassium permanganate (KMnO4, 6.0 g) was added. The reaction mixture was refluxed overnight under magnetic stirring. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming that the feedstock was completely consumed, the reaction mixture was filtered to remove the generated manganese dioxide (MnO2). The filtrate was concentrated to about 5 mL. Subsequently, the concentrate was acidified with 35% aqueous hydrochloric acid and the mixture was placed in a refrigerator overnight. The precipitated white precipitate was collected by filtration and washed several times with water to give 2,2'-bipyridine-5,5'-dicarboxylic acid (1.0 g, 74% yield) as a final white powder.
References
[1] Dalton Transactions, 2008, # 15, p. 2054 - 2060
[2] Journal of the American Chemical Society, 2012, vol. 134, # 2, p. 968 - 978
[3] Chemistry - A European Journal, 2012, vol. 18, # 23, p. 7030 - 7035
[4] Chemistry - A European Journal, 2013, vol. 19, # 40, p. 13369 - 13375
[5] Dalton Transactions, 2016, vol. 45, # 3, p. 881 - 885
