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
1. [1]
  Cordaro J G, McCusker J K, Bergman R G. Synthesis of Mono-substituted 2, 2'-Bipyridines[J]. Chem Commun, 2002,14:1496-1497.
2. [2]
  Bass P, Purdon R A, Patterson M A. Gastric Antisecretory and Other Pharmacologic Studies on 2, 2'-Bipyridine[J]. J Pharmacol Exp Ther, 1966,152(152):104-115.
3. [3]
  Kaes C, Katz A, Hosseini M W. Bipyridine:The Most Widely Used Ligand. A Review of Molecules Comprising at Least Two 2, 2'-Bipyridine Units[J]. Chem Rev, 2000,100(10):3553-3590. doi: 10.1021/cr990376z
4. [4]
  LI Haiyan, LI Yunhui, PAN Lihua. Preparation and Characterization of a Novel Type Complex[J]. Chinese J Appl Chem, 2010,27(9):1008-1011.
5. [5]
  Alpha B, Anklam E, Deschenaux R. Synthesis and Characterisation of the Sodium and Lithium Cryptates of Macrobicyclic Ligands Incorporating Pyridine, Bipyridine, and Biisoquinoline Units[J]. Helv Chim Acta, 1988,71:1042-1052. doi: 10.1002/(ISSN)1522-2675
6. [6]
  Penalva V, Hassan J, Lavenot L. Direct Homocoupling of Aryl Halides Catalyzed by Palladium[J]. Tetrahedron Lett, 1998,39:2559-2560. doi: 10.1016/S0040-4039(98)00196-8
7. [7]
  Tiecco M, Testaferri L, Tingoli M. A Convenient Synthesis of Bipyridines by Nickel-phosphine Complex-Mediated Homo Coupling of Halopyridines[J]. Synthesis, 1984,16(9):736-738.
8. [8]
  Vanderesse R, Lourak M, Fort Y. Activation of Reducing Agents. Sodium Hydride Containing Complex Reducing Agents 23.Symmetrical Coupling of Nitrogen-containing Heterocyclic Halides[J]. Tetrahedron Lett, 1986,27(45):5483-5486. doi: 10.1016/S0040-4039(00)85243-0
9. [9]
  Fort Y, Becker S, Caubere P. A Convenient Synthetic Route to Bis-heteroaromatic and Bis-heterocyclic Compounds Promoted by Liganded Nickel Complex Reducing Agents[J]. Tetrahedron, 1994,50(41):11893-11902. doi: 10.1016/S0040-4020(01)89303-0
10. [10]
  HONG Ran. Nickel Catalyst Ullmann Coupling Reaction of the Preliminary Study and Crystal Morphology Effect of the Hydrogen Acceptor in the Catalytic Transfer Hydrogenation[D]. Shanghai:Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 2001(in Chinese).
11. [11]
  QIAN Yanlong, WANG Chen, TAO Xiaochun. Synthesis of 2, 2'-Bipyridine Through Catalitic Coupling Reaction of α-Brompyridine Using Nickel Complex[J]. J Org Chem, 2003,23(11):1264-1266.
12. [12]
  Cornella J, Gómez-Bengoa E, Martin R. Combined Experimental and Theoretical Study on the Reductive Cleavage of Inert C-O Bonds with Silanes:Ruling out a Classical Ni (0)/Ni (Ⅱ) Catalytic Couple and Evidence for Ni (Ⅰ) Intermediates[J]. J Am Chem Soc, 2013,135(5):1997-2009. doi: 10.1021/ja311940s
13. [13]
  Lanni E L, McNeil A J. Mechanistic Studies on Ni (dppe) Cl₂-catalyzed Chain-growth Polymerizations:Evidence for Rate-determining Reductive Elimination[J]. J Am Chem Soc, 2009,131(45):16573-16579. doi: 10.1021/ja904197q
14. [14]
  Amatore C, Jutand A. Rates and Mechanism of Biphenyl Synthesis Catalyzed by Electrogenerated Coordinatively Unsaturated Nickel Complexes[J]. Organometallics, 1988,7(10):2203-2214. doi: 10.1021/om00100a019
15. [15]
  LI Zhe. Mechanisms of Palladium and Nickel Catalyzed Cross Coupling Reactions[D]. Hefei:University of Science and Technology of China, 2009(in Chinese).
1. [1]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
2. [2]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
3. [3]
  Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
4. [4]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
5. [5]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
6. [6]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
7. [7]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
8. [8]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
9. [9]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
10. [10]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
11. [11]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
12. [12]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
13. [13]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
14. [14]
  Ping Song , Nan Zhang , Jie Wang , Rui Yan , Zhiqiang Wang , Yingxue Jin . Experimental Teaching Design on Synthesis and Antitumor Activity Study of Cu-Pyropheophorbide-a Methyl Ester. University Chemistry, 2024, 39(6): 278-286. doi: 10.3866/PKU.DXHX202310087
15. [15]
  Ruoxi Sun , Yiqian Xu , Shaoru Rong , Chunmiao Han , Hui Xu . The Enchanting Collision of Light and Time Magic: Exploring the Footprints of Long Afterglow Lifetime. University Chemistry, 2024, 39(5): 90-97. doi: 10.3866/PKU.DXHX202310001
16. [16]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
17. [17]
  Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
18. [18]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
19. [19]
  Juntao Yan , Liang Wei . 2D S-Scheme Heterojunction Photocatalyst. Acta Physico-Chimica Sinica, 2024, 40(10): 2312024-. doi: 10.3866/PKU.WHXB202312024
20. [20]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(298)
HTML views(35)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142