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Synthesis of (3-Aminophenyl)(morpholino)methanone from Benzotrichloride as Precursor
Corresponding Author(s) : I.V. Kasi Viswanath
Asian Journal of Chemistry,
Vol. 28 No. 2 (2016): Vol 28 Issue 2
Abstract
(3-Aminophenyl)(morpholino)methanone derivatives are key intermediates in the preparation of active pharmaceutical ingredients. In this synthesis benzotrichloride is selected as a precursor for the preparation of target molecule, the precursor is easily available raw material. The present synthesis consisting of four steps, in the first step we are nitrating the benzotrichloride to obtain the meta-nitrobenzoic acid, which on chlorinated with thionyl chloride to obtain meta nitro benzoyl chloride, which on condensing with morpholine, further reduction with iron and HCl for the formation of the target molecule.
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References
J.U. Flanagan, G.J. Atwell, D.M. Heinrich, D.G. Brooke, S. Silva, L.J.M. Rigoreau, E. Trivier, A.P. Turnbull, T. Raynham, S.M.F. Jamieson and W.A. Denny, Bioorg. Med. Chem., 22, 967 (2014); doi:10.1016/j.bmc.2013.12.050.
F. Belluti, M. Bartolini, G. Bottegoni, A. Bisi, A. Cavalli, V. Andrisano and A. Rampa, Eur. J. Med. Chem., 46, 1682 (2011); doi:10.1016/j.ejmech.2011.02.019.
L. Antonioli, B. Csóka, M. Fornai, R. Colucci, E. Kókai, C. Blandizzi and G. Haskó, Drug Discov. Today, 19, 1051 (2014); doi:10.1016/j.drudis.2014.02.010.
O. Bruno, S. Schenone, A. Ranise, F. Bondavalli, E. Barocelli, V. Ballabeni, M. Chiavarini, S. Bertoni, M. Tognolini and M. Impicciatore, Bioorg. Med. Chem., 9, 629 (2001); doi:10.1016/S0968-0896(00)00272-8.
C.L. Yaws, Thermophysical Properties of Chemicals and Hydrocarbons, Elsevier, edn 2, p. 264 (2014).
C.L. Yaws, Thermophysical Properties of Chemicals and Hydrocarbons, Elsevier, edn 2, p. 496 (2014).
F.E.Dayan and M.L.M. Zaccaro, Pestic. Biochem. Physiol., 102, 189 (2012); doi:10.1016/j.pestbp.2012.01.005.
F.E. Dayan and S.B. Watson, Pestic. Biochem. Physiol., 101, 182 (2011); doi:10.1016/j.pestbp.2011.09.004.