Uses
4,4‘-Bis(hydroxymethyl)-2,2’-bipyridine is a replication inhibitor that has been used in the treatment of cancer. It has also been shown to be effective in the treatment of metabolic disorders and chronic bronchitis.
Synthesis
The general procedure for the synthesis of 2,2'-bipyridine-4,4'-dimethanol from diethyl [2,2'-bipyridine]-4,4'-dicarboxylate was as follows: sodium borohydride (1.87 g, 49 mmol) was added to diethyl [2,2'-bipyridine]-4,4'-dicarboxylate (567 mg) dissolved in anhydrous ethanol (34 mL) , 1.89 mmol) suspension. The reaction mixture was refluxed for 3 hours. After completion of the reaction, it was cooled to room temperature and saturated ammonium chloride solution (24 mL/g NH4Cl) was added to quench the excess sodium borohydride. Subsequently, ethanol was removed by evaporation under reduced pressure. The resulting solid was dissolved in a minimal amount of water using an ultrasonic bath. The aqueous phase was extracted with ethyl acetate (5 x 34 mL) and the organic phases were combined and dried over anhydrous sodium sulfate. Finally, the organic phase was concentrated under reduced pressure to give a white powdery product in 91% yield.
References
[1] Chemical Communications, 2009, # 48, p. 7545 - 7547
[2] Electrochimica Acta, 2016, vol. 207, p. 313 - 320
[3] Journal of Physical Chemistry B, 1999, vol. 103, # 38, p. 8067 - 8079
[4] Patent: CN105793241, 2016, A. Location in patent: Paragraph 0129; 0159
[5] Tetrahedron, 2014, vol. 70, # 36, p. 6271 - 6275
