A Novel Synthetic Method for 1-(2,4-Dichlorophenyl)-4-methyl- 5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic Acid

doi:10.6023/cjoc201210032

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 607-610.DOI: 10.6023/cjoc201210032 Previous Articles Next Articles

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1-(2,4-二氯苯基)-4-甲基-5-(4-氯苯基)吡唑-3-羧酸的新合成方法

杨照^a, 王志祥^a, 方正^b, 郭凯^b

a 中国药科大学药学院南京 210009;
b 南京工业大学药学院南京 210009

收稿日期:2012-10-17 修回日期:2012-11-23 发布日期:2012-11-26
通讯作者: 王志祥 E-mail:zhixwang@163.com
基金资助:
国家重点基础研究发展计划(973计划, Nos. 2012CB725204, 2012CB721104)资助项目.

A Novel Synthetic Method for 1-(2,4-Dichlorophenyl)-4-methyl- 5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic Acid

Yang Zhao^a, Wang Zhixiang^a, Fang Zheng^b, Guo Kai^b

a College of Pharmacy, China Pharmaceutical of University, Nanjing 210009;
b School of Pharmaceutical Science, Nanjing University of Technology, Nanjing 210009

Received:2012-10-17 Revised:2012-11-23 Published:2012-11-26
Supported by:
Project supported by the National Key Basic Research Program of China (973 Program) (Nos. 2012CB725204, 2012CB721104).

A novel method for the synthesis of 1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carbox- ylic acid was reported. The target compound was prepared starting from 4-chlorobenzaldehyde, which is inexpensive and easily available starting material, via adol condensation, cyclization and oxidation with the total yield of 50.6%. The structures of intermediates and final product were determined by ¹H NMR and MS. The novel method with the advantages of shorten process, easily conducted procedure and relatively high yield is suitable for scale-up production.

Key words: 1,5-diarylpyrazole, phenyl hydrazone, cyclization, oxidation, synthesis

Cite this article

Yang Zhao, Wang Zhixiang, Fang Zheng, Guo Kai. A Novel Synthetic Method for 1-(2,4-Dichlorophenyl)-4-methyl- 5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic Acid[J]. Chin. J. Org. Chem., 2013, 33(03): 607-610.

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References

[1] (a) Munro, S.; Thomas, K. L.; Abu-Shaar, M. Nature 1993, 365, 61.
(b) Kyrou, I.; Valsamakis, G.; Tsigos, C. Ann. N. Y. Acad. Sci. 2006, 1083, 270.

[2] Akbas, F.; Gasteyger, C.; Sjödin, A.; Astrup, A.; Larsen, T. M. Obes. Rev. 2009, 10, 58.

[3] VanGaal, L. F.; Rissanen, A. M.; Scheen, A. J.; Ziegler, O.; Rossner, S. Lancet 2005, 365, 1387.

[4] (a) Vazquez, N.; Gomez-Vallejo, V.; Llop, J. Tetrahedron. Lett. 2012, 53, 4743.
(b) Tu, G. G.; Xiong, F.; Huang, H. M.; Kuang B. H.; Li, S. H. J. Enzyme Inhib. Med. Chem. 2011, 26, 222.
(c) Sasmal, P. K.; Reddy, D. S.; Talwar, R.; Venkatesham, B.; Balasubrahmanyam, D.; Kannan, M.; Srinivas, P.; Kumar, K. S.; Devi, B. N.; Jadhav, V. P.; Khan, S. K.; Mohan, P.; Chaudhury, H.; Bhuniya, D.; Iqbal, J.; Chakrabarti, R. Bioorg. Med. Chem. Lett. 2011, 21, 562.
(d) Wu, C.; Hung, M.; Song, J.; Yeh, T.; Chou, M.; Chu, C.; Jan, J.; Hsieh, M.; Tseng, S.; Chang, C.; Hsieh, W.; Lin, Y.; Yeh, Y.; Chung, W.; Kuo, C.; Lin, C.; Shy, H.; Chao, Y.; Shia, K. J. Med. Chem. 2009, 52, 4496.

[5] (a) Dutta, A. K.; Sard, H.; Ryan, W.; Razdan, R. K.; Compton, D. R.; Martin, B. R. Med. Chem. Res. 1995, 5, 54.
(b) Barth, F.; Casellas, P.; Congy, C.; Martinez, S.; Rinaldi, M.; Ann-Archard, G. EP 656354, 1994 [Chem. Abstr. 1994, 123, 286006].
(c) Tang, L.-H.; Tao, L.; Chen, H.-B.; Zhong, B.-H. Chin. J. Pharm. 2007, 38, 252 (in Chinese).
(汤立合, 陶林, 陈合兵, 仲伯华, 中国医药工业杂志, 2007, 38, 252.)
(d) Kotagiri, V. K.; Suthrapu, S.; Reddy, J. M.; Rao, C. P.; Bollugoddu, V.; Bhattacharya, A.; Bandichhor, R. Org. Process Res. Dev. 2007, 11, 910.
(e) Nerdinger, S. WO 2008101860, 2008 [Chem. Abstr. 2008, 149, 307838].
(f) Jin, W.-H.; Zhang, P.-Z.; Ji, Y.-F. Chin. J. Synth. Chem. 2010, 18, 397 (in Chinese).
(金文虎, 张鹏志, 冀亚飞, 合成化学, 2010, 18, 397. )

[6] Donohue, S. R.; Halldin, C.; Pike, V. W. Tetrahedron Lett. 2008, 49, 2789.

[7] Gomez, G. M.; Conde Jimenez, J. L.; Podio Lora, V. An. Quim.; Ser. C 1986, 82, 204.

[8] Stroh, H. H.; Lamprecht, H. Chem. Ber. 1963, 96, 651.

[9] Foye, W. O. J. Pharm. Sci. 1979, 68, 591.

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1-(2,4-二氯苯基)-4-甲基-5-(4-氯苯基)吡唑-3-羧酸的新合成方法

A Novel Synthetic Method for 1-(2,4-Dichlorophenyl)-4-methyl- 5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic Acid

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