PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2011 | 9 | 4 | 590-597
Article title

Facile dehalogenation of halogenated anilines and their derivatives using Al-Ni alloy in alkaline aqueous solution

Content
Title variants
Languages of publication
EN
Abstracts
EN
This article describes the simple hydrodehalogenation of halogenated anilines and their derivatives by the action of Raney aluminium-nickel alloy in aqueous alkaline solution at room temperature. The reaction course was monitored by means of 1H nuclear magnetic resonance (NMR) spectroscopy and GC-MS spectra. [...] The effect of Al and Ni and the nature and quantity of the base for effective hydrodehalogenation were studied. The possibility of lowering Al content more than 500 times and Ni content more than 10 times in the filtered mother liquor by a dehalogenation procedure was tested using precipitation. The reduction method described was satisfactorily proved for dehalogenation of polyhalogenated anilines in the multiphase dimethoxymethane/aqueous NaOH/Al-Ni reaction mixture. Dehalogenation under multi-phase conditions was demonstrated for the preparation of ortho-alkylated anilines from simply available 2-substituted-4-chloroanilines.
Publisher
Journal
Year
Volume
9
Issue
4
Pages
590-597
Physical description
Dates
published
1 - 8 - 2011
online
4 - 6 - 2011
References
  • [1] F. Effenberger, Angew. Chem., Int. Ed. 41, 1699 (2002) http://dx.doi.org/10.1002/1521-3773(20020517)41:10<1699::AID-ANIE1699>3.0.CO;2-N[Crossref]
  • [2] V.V. Grushin, Acc. Chem. Res. 26, 279 (1993) http://dx.doi.org/10.1021/ar00029a009[Crossref]
  • [3] H.Y. Choi, D.Y. Chi, J. Am. Chem. Soc. 123, 9202 (2001) http://dx.doi.org/10.1021/ja0164374[Crossref]
  • [4] M.H. Block, S. Boyer, W. Brailsford, D.R. Brittain, D. Carroll, S. Chapman, D.S Clarke, C.S. Donald, K.M. Foote, L. Godfrey, A. Ladner, P.R. Marsham, D.J. Masters, C.D. Mee, M.R. O’Donovan, J.E. Pease, A.G. Pickup, J.W. Roberts, A. Rayner, P. Schofield, A. Suleman, A.V. Turnbull, J. Med. Chem. 45, 3509 (2002) http://dx.doi.org/10.1021/jm011125x[Crossref]
  • [5] The Merck Index, An Encyclopedia of Chemicals, Drugs and Biologicals (Merck&Co., Inc., NI-159, New York, 1996) 640, 1209, 1239
  • [6] E.C. Cortés, R.S. Franco, O.G. Mellado, J. Heterocyclic Chem. 38, 663 (2001) http://dx.doi.org/10.1002/jhet.5570380320[Crossref]
  • [7] L.T. Kaspar, B. Fingerhut, L. Ackermann, Angew. Chem., Int. Ed. 44, 5972 (2005) http://dx.doi.org/10.1002/anie.200501423[Crossref]
  • [8] N. Seshu Babu, K. Mohan Reddy, P.S. Sai Prasad, I. Suryanarayana, N. Lingaiah, Tetrahedron Lett. 48, 7642 (2007) http://dx.doi.org/10.1016/j.tetlet.2007.08.120[Crossref]
  • [9] A. Arienti, F. Bigi, R. Maggi, E. Marzi, P. Moggi, Tetrahedron 53, 3795 (1997) http://dx.doi.org/10.1016/S0040-4020(97)00100-2[Crossref]
  • [10] X.-T. Huang, Z.-Y. Long, Q.-Y. Chen, J. Fluorine Chem. 111, 107 (2001) http://dx.doi.org/10.1016/S0022-1139(01)00442-0[Crossref]
  • [11] S.H. Yalkowsky, Y. He, Handbook of Aqueous Solubility Data (CRC Press, Boca Raton, Florida, 2003) 244 http://dx.doi.org/10.1201/9780203490396[Crossref]
  • [12] C. Tixier, M. Sancelme, F. Bonnemoy, A. Cuer, N. Truffaut, H. Veschambre, Environ. Toxicol. Chem. 20, 1381 (2001) http://dx.doi.org/10.1002/etc.5620200701[Crossref]
  • [13] F. Massicot, R. Schneider, Y. Fort, S. Illy-Cherrey, O. Tillement, Tetrahedron 56, 4765 (2000) http://dx.doi.org/10.1016/S0040-4020(00)00383-5[Crossref]
  • [14] F. Alonso, I.P. Beletskaya, M. Yus, Chem. Rev. 102, 4009 (2002) http://dx.doi.org/10.1021/cr0102967[Crossref]
  • [15] G.-B. Liu, H.-Y. Zhao, B. Yang, T. Thiemann, Green Chem. Lett. Rev. 3, 1 (2010) http://dx.doi.org/10.1080/17518250903393882[Crossref]
  • [16] V. Dichiarante, M. Fagnoni, A. Albini, Green Chem. 11, 942 (2009) http://dx.doi.org/10.1039/b904897a[Crossref]
  • [17] X. Xu, H. Zhou, M. Zhou, Chemosphere 62(5), 847 (2006) http://dx.doi.org/10.1016/j.chemosphere.2005.04.073[Crossref]
  • [18] G. Lunn, E.B. Sansone, AIHA Journal 52, 252 (1991) http://dx.doi.org/10.1080/15298669191364686[Crossref]
  • [19] L.K. Keefer, G. Lunn, Chem. Rev. 89, 459 (1989) http://dx.doi.org/10.1021/cr00093a002[Crossref]
  • [20] G.-B. Liu, L. Dai, X. Gao, M.-K. Li, T. Thiemann, Green Chem. 8, 781 (2006) http://dx.doi.org/10.1039/b605261d[Crossref]
  • [21] G.-B. Liu, L. Dai, X. Gao, M.K. Li, T. Thiemann, Tetrahedron 65(12), 2497 (2009) http://dx.doi.org/10.1016/j.tet.2009.01.052[Crossref]
  • [22] T. Weidlich, A. Krejčová, L. Prokeš, Monats. Chem. 141, 1015 (2010) http://dx.doi.org/10.1007/s00706-010-0362-9[Crossref]
  • [23] A.H.M. Veeken, W.H. Rulkens, Water Sci. Technol. 47(10), 9 (2003)
  • [24] T.S. Roetting, J. Cama, C. Ayora, J.L. Cortina, J. De Pablo, Environ. Sci. Technol. 40, 6438 (2006) http://dx.doi.org/10.1021/es061092g[Crossref]
  • [25] J.Y. Lee, S.V. Rao, B.N. Kumar, D.J. Kang, B.R. Reddy, J. Hazard. Mater. 176, 1122 (2010) http://dx.doi.org/10.1016/j.jhazmat.2009.11.137[Crossref]
  • [26] A. Agueera, E. Almansa, A. Tejedor, A.R. Fenrandez-Alba, S. Malato, M.I. Maldonado, Environ. Sci. Technol. 34, 1563 (2000) http://dx.doi.org/10.1021/es990112u[Crossref]
  • [27] D. Quo, H. Huang, H. Jiang, H. Liu, J. Xu, Org. Lett. 10, 4513 (2008) http://dx.doi.org/10.1021/ol801784a[Crossref]
  • [28] G. Manolikates, M.A. Schade, A. Metzger, P. Knochel, C. Munoz Hernandez, J. Org. Chem. 73, 8422 (2008) http://dx.doi.org/10.1021/jo8015852[Crossref]
  • [29] M. Tordeux, B. Langlois, C.J. Wakselman, Chem. Soc., Perkin Trans. 1,8, 2293 (1990) [Crossref]
  • [30] C.R. Gannelin, D.J. Triggle, Dictionary of pharmacological agents 1–2 (Chapman and Hall, London, 1996) 663
  • [31] G.-B. Liu, H.-Y. Zhao, B. Yang, T. Thiemann, Green Chem. Lett. Rev. 3, 1 (2010) http://dx.doi.org/10.1080/17518250903393882[Crossref]
  • [32] B.H. Lipschutz, S. Tasler, Adv. Synth. Catal. 343, 327 (2001) http://dx.doi.org/10.1002/1615-4169(20010430)343:4<327::AID-ADSC327>3.0.CO;2-R[Crossref]
  • [33] T. Janiak, J. Blazejowski, Chemosphere 48,1097 (2002) http://dx.doi.org/10.1016/S0045-6535(02)00155-8[Crossref]
  • [34] C.J.H. Miermans, L.E. van der Velde, P.C.M. Frintrop, Chemosphere 40, 39 (2000) http://dx.doi.org/10.1016/S0045-6535(99)00229-5[Crossref]
  • [35] W. Tsuzuki, A. Ue, A. Nagao, Biosci. Biotechnol. Biochem. 67, 1660 (2003) http://dx.doi.org/10.1271/bbb.67.1660[Crossref]
  • [36] H.E. Seifried, R.M. Seifried, J.J. Clarke, T.B. Junghans, R.H.C. San, Chem. Res. Toxicol. 19, 627 (2006) http://dx.doi.org/10.1021/tx0503552[Crossref]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-011-0033-7
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.