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Synthesis of 2-(arylamino)nicotinic acids in high-temperature water

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Abstract

In hydrothermal reactions at 150–180 °C, 2-(arylamino)nicotinic acids were synthesized by amination of 2-chloronicotinic acid with aromatic amine derivatives, with potassium carbonate as base. The procedure is efficient, environmentally friendly, and practical, with moderate to excellent yields (up to 98%).

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References

  1. N. Akiya, P.E. Savage, Chem. Rev. 102, 2725–2750 (2002)

    Article  CAS  Google Scholar 

  2. M. Sasaki, B. Kabyemela, R. Malaluan, S. Hirose, N. Takeda, T. Adschiri, K. Arai, J. Supercrit. Fluids 13, 261–268 (1998)

    Article  CAS  Google Scholar 

  3. N.A. Rebacz, P.E. Savage, Ind. Eng. Chem. Res. 49, 535–540 (2010)

    Article  CAS  Google Scholar 

  4. Z. Shen, Y. Zhang, F. Jin, X. Zhou, A. Kishita, K. Ind, Eng. Chem. Res. 49, 6255–6259 (2010)

    Article  CAS  Google Scholar 

  5. J. Fraga-Dubreuil, J. Garcia-Serna, E. Garcia-Verdugo, L.M. Dudd, G.R. Aird, W.B. Thomas, M. Poliakoff, J. Supercrit. Fluids 39, 220–227 (2006)

    Article  CAS  Google Scholar 

  6. T. Hirashita, S. Kuwahara, S. Okochi, M. Tsuji, S. Araki, Tetrahedron Lett. 51, 1847–1851 (2010)

    Article  CAS  Google Scholar 

  7. K. Chandler, F. Deng, A.K. Dillow, C.L. Liotta, C.A. Eckert, Ind. Eng. Chem. Res. 36, 5175–5179 (1997)

    Article  CAS  Google Scholar 

  8. L.U. Gron, A.S. Tinsley, Tetrahedron Lett. 40, 227–230 (1999)

    Article  CAS  Google Scholar 

  9. C.J. Li, Angew. Chem. Int. Ed. 42, 4856–4858 (2003)

    Article  CAS  Google Scholar 

  10. D.J. Jang, J.S. Park, H.R. Ko, J.P. Jee, J.K. Kim, S.T. Kim, C.K. Kim, Biomed. Chromatogr. 19, 32–35 (2005)

    Article  CAS  Google Scholar 

  11. M.T. Cocco, C. Congiu, V. Onnis, M. Morelli, V. Felipo, O. Cauli, Bioorg. Med. Chem. 12, 4169–4177 (2004)

    Article  CAS  Google Scholar 

  12. H. Ban, M. Muraoka, N. Ohashi, Tetrahedron 61, 10081–10092 (2005)

    Article  CAS  Google Scholar 

  13. H. Ban, M. Muraoka, N. Ohashi, Tetrahedron Lett. 44, 6021–6023 (2003)

    Article  CAS  Google Scholar 

  14. M.H. Sherlock, J.J. Kaminski, W.C. Tom, J.F. Lee, S.C. Wong, W. Kreutner, R.W. Bryant, A.T. McPhail, J. Med. Chem. 31, 2108–2121 (1988)

    Article  CAS  Google Scholar 

  15. W.A. Denny, G.J. Atwell, B.F. Cain, J. Med. Chem. 20, 1242–1246 (1977)

    Article  CAS  Google Scholar 

  16. C. Afloroaei, M. Vlassa, A. Becze, P. Brouant, J. Barbe, Heterocycl. Commun. 5, 249–252 (1999)

    Article  CAS  Google Scholar 

  17. H. Misbahi, P. Brouant, J. Barbe, Heterocycl. Commun. 9, 335–336 (2003)

    Article  CAS  Google Scholar 

  18. N.B. Patel, S.N. Agravat, Chin. J. Chem. 25, 1363–1369 (2007)

    Article  CAS  Google Scholar 

  19. Y.L. Chen, R.S. Obach, J. Braselton, M.L. Corman, J. Forman, J. Freeman, R.J. Gallaschun, R. Mansbach, A.W. Schmidt, J.S. Sprouse, F.D. Tingley III, E. Winston, D.W. Schulz, J. Med. Chem. 51, 1385–1392 (2008)

    Article  CAS  Google Scholar 

  20. S. Long, S. Parkin, M.A. Siegler, A. Cammers, T. Li, Cryst. Growth Des. 8, 4006–4013 (2008)

    Article  CAS  Google Scholar 

  21. S. Long, T. Li, Cryst. Growth Des. 9, 4993–4997 (2009)

    Article  CAS  Google Scholar 

  22. C.E. Quevedo, V. Bavetsias, E. McDonald, Tetrahedron Lett. 50, 2481–2483 (2009)

    Article  CAS  Google Scholar 

  23. K.M. Ghoneim, Egypt J. Pharm. Sci. 28, 9–16 (1987)

    CAS  Google Scholar 

  24. F.G. Mann, J. Chem. Soc. 2057–2062 (1952)

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Acknowledgment

We thank the Ministry of Science and Technology of China (no. 2010DFA32680) for their generous financial support.

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Authors and Affiliations

  1. College of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030, People’s Republic of China

    Zhenghua Li, Shangyou Xiao, Ronghui Liang & Zhining Xia

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  1. Zhenghua Li
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  2. Shangyou Xiao
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  3. Ronghui Liang
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  4. Zhining Xia
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Correspondence to Zhining Xia.

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Li, Z., Xiao, S., Liang, R. et al. Synthesis of 2-(arylamino)nicotinic acids in high-temperature water. Res Chem Intermed 38, 1691–1697 (2012). https://doi.org/10.1007/s11164-012-0494-0

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  • DOI: https://doi.org/10.1007/s11164-012-0494-0

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