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Synthesis of Diethyl 5-Ethyl-2,3-Pyridinedicarboxylate
Corresponding Author(s) : Chunsheng Cheng
Asian Journal of Chemistry,
Vol. 26 No. 3 (2014): Vol 26 Issue 3
Abstract
Diethyl 5-ethyl-2,3-pyridinedicarboxylate was synthesized using ammonium acetate as the nitrogen source. The optimum process conditions were obtained by exploring the reaction mechanism and researching the effects of reactant ratio, reaction temperature and solvent amount on the yield from all sides. Diethyl 5-ethyl-2,3-pyridinedicarboxylate yield was 98 % analysis by HPLC and the overall yield 96.8 % calculated by 2-chloro-3-oxo-succinic acid diethyl ester. The optimum process has the advantages of available initial material, simple waste-water treatment and environmental friendliness which are more applicable for industrial production.
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- A.N. Vasiliev, A.F. Lopez, J.D. Fernandez and A.J. Mocchi, Molecules, 9, 535 (2004); doi:10.3390/90700535.
- P.J. Wepplo, Pestic. Sci., 29, 293 (1990); doi:10.1002/ps.2780290306.
- A.N. Vasiliev, A.F. Lopez and A.J. Mocchi, Molecules, 5, 338 (2000); doi:10.3390/50300338.
- M. Los, Ortho-(5-oxo-2-imidazolin-2-yl)arylcarboxylates-a new class of herbicides, In Pesticide synthesis through rational approaches, American Chemical Society:Washington, D.C, pp. 29-44 (1984).
- M. Los, Synthesis and biology of the imidazolinone herbicides, In Proceedings of the 6th international congress of pesticide chemistry(Ottawa, Aug. 10-15, 1986), Greenhaugh R, Roberts TR, Eds, Blachwell scientific pub: Oxford, UK, pp. 35-42 (1987).
- P.J. Wepplo, Process for the preparation of pyridyl and quinolyl imidazolinones, US Patent 4474962 (1984).
- D.R. Maulding and R.F. Doehner, Process for the preparation of 2-(5-isopropyl-5- methyl-4-oxo-2-imidazolin-2-yl)-3-quinoline-carboxylic acid and alkyl 2-trichloromethyl- 3-quinolinecarboxylate intermediates therefor, US Patent 4459408 (1984).
- M. Los, 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicide agents, US Patent 4798619 (1989).
- Y.L. Liu and B.G. Ma, Modern Agrochem., 2, 17 (2011).
- Y.L. Liu and B.G. Ma, Pestic. Sci. Admin, 32, 23 (2011).
- J. Saukaitis, East Greenwich RI, US Patent 5808067 (1998).
- V. Elango, M.P. Bodman and D.R. Larkin, EP Patent 0452094A2 (1991).
- G.A. Chiarello, EP Patent 0548559A1 (1892).
- Y. Takaharu, K. Mitsuhiro and S. Shouzo, EP 0274379A (1988); B.F. Gupton, US Patent 5208342 (1993).
- Z.M. Cheng, Shanghai Chem. Ind., 34, 22 (2009).
- Q.H. Tang and Y.B. Zhang, Shanghai Chem. Ind., 13, 31 (2009).
- Z.M. Cheng and B.Q. Gu, Agrochemicals, 40, 9 (2001).
- Zhou Y, 1, 41 (1997).
- D.F. Ji, Y.C. Wang, Z.Y. Geng, M.Y. La and W.P. Ma, Sci. Sinica Chim., 42, 815 (2012); doi:10.1360/032011-429.
- F.C. Zeng, Inorg. Chem. Ind., 9, 1 (2009).
- G.Z. Hu, G.C. Xu and L.T. Gao, Technol. Testing, 5, 49 (2002).
- L.S. Tian, Chem. Eng., 3, 10 (1992).
References
A.N. Vasiliev, A.F. Lopez, J.D. Fernandez and A.J. Mocchi, Molecules, 9, 535 (2004); doi:10.3390/90700535.
P.J. Wepplo, Pestic. Sci., 29, 293 (1990); doi:10.1002/ps.2780290306.
A.N. Vasiliev, A.F. Lopez and A.J. Mocchi, Molecules, 5, 338 (2000); doi:10.3390/50300338.
M. Los, Ortho-(5-oxo-2-imidazolin-2-yl)arylcarboxylates-a new class of herbicides, In Pesticide synthesis through rational approaches, American Chemical Society:Washington, D.C, pp. 29-44 (1984).
M. Los, Synthesis and biology of the imidazolinone herbicides, In Proceedings of the 6th international congress of pesticide chemistry(Ottawa, Aug. 10-15, 1986), Greenhaugh R, Roberts TR, Eds, Blachwell scientific pub: Oxford, UK, pp. 35-42 (1987).
P.J. Wepplo, Process for the preparation of pyridyl and quinolyl imidazolinones, US Patent 4474962 (1984).
D.R. Maulding and R.F. Doehner, Process for the preparation of 2-(5-isopropyl-5- methyl-4-oxo-2-imidazolin-2-yl)-3-quinoline-carboxylic acid and alkyl 2-trichloromethyl- 3-quinolinecarboxylate intermediates therefor, US Patent 4459408 (1984).
M. Los, 2-(2-imidazolin-2-yl)-pyridines and quinolines and use of said compounds as herbicide agents, US Patent 4798619 (1989).
Y.L. Liu and B.G. Ma, Modern Agrochem., 2, 17 (2011).
Y.L. Liu and B.G. Ma, Pestic. Sci. Admin, 32, 23 (2011).
J. Saukaitis, East Greenwich RI, US Patent 5808067 (1998).
V. Elango, M.P. Bodman and D.R. Larkin, EP Patent 0452094A2 (1991).
G.A. Chiarello, EP Patent 0548559A1 (1892).
Y. Takaharu, K. Mitsuhiro and S. Shouzo, EP 0274379A (1988); B.F. Gupton, US Patent 5208342 (1993).
Z.M. Cheng, Shanghai Chem. Ind., 34, 22 (2009).
Q.H. Tang and Y.B. Zhang, Shanghai Chem. Ind., 13, 31 (2009).
Z.M. Cheng and B.Q. Gu, Agrochemicals, 40, 9 (2001).
Zhou Y, 1, 41 (1997).
D.F. Ji, Y.C. Wang, Z.Y. Geng, M.Y. La and W.P. Ma, Sci. Sinica Chim., 42, 815 (2012); doi:10.1360/032011-429.
F.C. Zeng, Inorg. Chem. Ind., 9, 1 (2009).
G.Z. Hu, G.C. Xu and L.T. Gao, Technol. Testing, 5, 49 (2002).
L.S. Tian, Chem. Eng., 3, 10 (1992).