Citation: CHAI Yongzhen, CHANG Yu, SONG Ruiqin, LIU Wei, LI Yunhui, PAN Lihua. Synthesis and Characterization of Dimethyl 6, 6'-Dimethyl-[2, 2'-bipyridine]-4, 4'-dicarboxylate[J]. Chinese Journal of Applied Chemistry, ;2017, 34(2): 146-150. doi: 10.11944/j.issn.1000-0518.2017.02.160163 shu

Synthesis and Characterization of Dimethyl 6, 6'-Dimethyl-[2, 2'-bipyridine]-4, 4'-dicarboxylate

CHAI Yongzhen ^a ,
CHANG Yu ^b ,
SONG Ruiqin ^a ,
LIU Wei ^a ,
LI Yunhui ^a,*,, ,
PAN Lihua ^b,*,,

a.
College of Chemical and Environmental Engineering, Changchun University of Science and Technology, Changchun 130022, China
b.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China

Corresponding author: LI Yunhui, liyh@cust.edu.cn PAN Lihua, lihuap@ciac.ac.cn
Received Date: 15 April 2016
Revised Date: 17 June 2016
Accepted Date: 5 July 2016

Fund Project: the Project of Jilin Provincial Development and Reform Commission 2014Y115the Key Science and Technology Project of Jilin Province 20150204010YY

Figures(4)

Dimethyl 6, 6'-dimethyl-[2, 2'-bipyridine]-4, 4'-dicarboxylate was synthesized in two steps from methyl 6-methyl-2-hydroxypyridine-4-carboxylate. The first step was the preparation of methyl 2-methyl-6-[(p-toluenesulfonyl) oxy]pyridine-4-carboxylate by esterification. The second step was to prepare the target product by nickel complex catalyzed homocoupling reaction. Several other factors which affected the reaction such as material proportion, reaction temperature and addition order were investigated. When the reaction was carried out under the optimal conditions, 77% yield was achieved. The products were characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectrometer (FTIR), mass spectrometry (MS) and differential scanning calorimetry (DSC) to prove the reliability of the synthetic method. This structure can fully satisfy the need of chelating agent intermediate for homogeneous time-resolved fluoroimmunoassay (HTRF), which has been succeeded in prectical applications.
- homogeneous time-resolved fluoroimmunoassay,
- homocoupling,
- dimethyl dimethyl-[bipyridine]-dicarboxylate
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