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Synthesis, Characterization and Crystal Structure of Methyl 4-(Benzyloxy)-5-methoxy-2-nitrobenzoate
Corresponding Author(s) : Li Fan
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
Methyl 4-(benzyloxy)-5-methoxy-2-nitrobenzoate was synthesized from 4-hydroxy-3-methoxybenzoic acid. Firstly, 4-hydroxy-3-methoxybenzoic acid reacted with methanol in the presence of concentrated sulfuric acid at reflux temperature, then the product of the first step was transformed into benzyl bromide by the process of substitution reaction by using K2CO3. Finally, the product was obtained by nitration reaction with HNO3. The product was characterized by 1H NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The results indicated that compound I crystallized in the monoclinic system, space group P2(1)/c with a = 5.590(2), b = 17.591 (7), c = 15.427(6) Å, V = 1516.9 (10) Å3; Z 4.
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- H. Takeda, N. Takigawa, K. Ohashi, D. Minami, I. Kataoka, E. Ichihara, N. Ochi, M. Tanimoto and K. Kiura, Exp. Cell Res., 319, 417 (2013); doi:10.1016/j.yexcr.2012.12.018.
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References
H. Takeda, N. Takigawa, K. Ohashi, D. Minami, I. Kataoka, E. Ichihara, N. Ochi, M. Tanimoto and K. Kiura, Exp. Cell Res., 319, 417 (2013); doi:10.1016/j.yexcr.2012.12.018.
L.F. Hennequin, E.S.E. Stokes, A.P. Thomas, C. Johnstone, P.A. Plé, D.J. Ogilvie, M. Dukes, S.R. Wedge, J. Kendrew and J.O. Curwen, J. Med. Chem., 45, 1300 (2002); doi:10.1021/jm011022e.
D. Zampieri, M. Grazia Mamolo, E. Laurini, C. Zanette, C. Florio, S. Collina, D. Rossi, O. Azzolina and L. Vio, Eur. J. Med. Chem., 44, 124 (2009); doi:10.1016/j.ejmech.2008.03.011.
Y. Seimbille, M.E. Phelps, J. Czernin and D.H.S. Silverman, J. Label. Comp. Radiopharm., 48, 829 (2005); doi:10.1002/jlcr.998.
S. Tasler, O. Muller, T. Wieber, T. Herz, S. Pegoraro, W. Saeb, M. Lang, R. Krauss, F. Totzke, U. Zirrgiebel, J.E. Ehlert, M.H.G. Kubbutat and C. Schächtele, Bioorg. Med. Chem., 17, 6728 (2009); doi:10.1016/j.bmc.2009.07.047.
T. Wang, A.S. Lui and I.S. Cloudsdale, Org. Lett., 1, 1835 (1999); doi:10.1021/ol991100g.
A. Kamal, N. Markandeya, N. Shankaraiah, C.R. Reddy, S. Prabhakar, C.S. Reddy, M.N. Eberlin and L. Silva Santos, Chem. Eur. J., 15, 7215 (2009); doi:10.1002/chem.200900853.
L.F. Hennequin, A.P. Thomas, C. Johnstone, E.S.E. Stokes, P.A. Plé, J.-J.M. Lohmann, D.J. Ogilvie, M. Dukes, S.R. Wedge, J.O. Curwen, J. Kendrew and C. Lambert-van der Brempt, J. Med. Chem., 42, 5369 (1999); doi:10.1021/jm990345w.