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An Innovative Approach for the Synthesis of 7-Hydroxyquinolin-2(1H)-one: A Key Intermediate of Brexpiprazole
Corresponding Author(s) : T. Ram Reddy
Asian Journal of Chemistry,
Vol. 30 No. 4 (2018): Vol 30 Issue 4
Abstract
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) mediated oxidation of 7-hydroxy-1,2,3,4-tetrahydro-2-quinolinone has been prepared from 3-hydroxy aniline to obtain 7-hydroxyquinolin-2(1H)-one in aqueous media. Stoichiometric quantities of DDQ and THF provides a high out put of 7-hydroxyquinolin-2(1H)-one and reduces the consumption of organic solvents and discourages by-products. Overall advantage with this approach was reduce the time cycle and cost of the brexpiprazole intermediate.
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- C.U. Correll, A. Skuban, J. Ouyang, M. Hobart, S. Pfister, R.D. McQuade, M. Nyilas, W.H. Carson, R. Sanchez and H. Eriksson, Am. J. Psych., 172, 870 (2015); https://doi.org/10.1176/appi.ajp.2015.14101275.
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References
C.U. Correll, A. Skuban, J. Ouyang, M. Hobart, S. Pfister, R.D. McQuade, M. Nyilas, W.H. Carson, R. Sanchez and H. Eriksson, Am. J. Psych., 172, 870 (2015); https://doi.org/10.1176/appi.ajp.2015.14101275.
K. Maeda, L. Lerdrup, H. Sugino, H. Akazawa, N. Amada, R.D. McQuade, T.B. Stensbøl, C. Bundgaard, J. Arnt and T. Kikuchi, J. Pharmacol. Exp. Ther., 350, 605 (2014); https://doi.org/10.1124/jpet.114.213819.
S. Frye, J. Jin and B. Roth, Functionally Selective Ligands of Dopamine d2 Receptors, WO 2012003418 (2012).
J.E. Campbell and P. Jones, Triazolo-Pyrazine Derivatives Useful in the Treatment of Disorders of the Central Nervous System, WO 2014085284 (2014).
T.-C. Wang, Y.-L. Chen, K.-H. Lee and C.-C. Tzeng, Synthesis, 87 (1997); https://doi.org/10.1055/s-1997-1505.
Z.-Y. Yang, Y. Xia, P. Xia, A. Brossi and K.-H. Lee, Tetrahedron Lett., 40, 4505 (1999); https://doi.org/10.1016/S0040-4039(99)00821-7.
R. Farina, L. Pisani, M. Catto, O. Nicolotti, D. Gadaleta, N. Denora, R. Soto-Otero, E. Mendez-Alvarez, C.S. Passos, G. Muncipinto, C.D. Altomare, A. Nurisso, P.-A. Carrupt and A. Carotti, J. Med. Chem., 58, 5561 (2015); https://doi.org/10.1021/acs.jmedchem.5b00599.
R. Friesen, R.N. Young, Y. Girard, M. Blouin and D. Dube, Heteroaryl Quinolines as Inhibitors of Leukotriene Biosynthesis, US Patent 5410054A (1993).
C.-C. Tzeng, Y.-L. Chen, T.-C. Wang, K.-C. Fang and N.-C. Chang, Heterocycles, 50, 453 (1999); https://doi.org/10.3987/COM-98-S(H)11.
R.M.A. El-Aal and A.I.M. Koraierm, J. Chin. Chem. Soc., 47, 389 (2000); https://doi.org/10.1002/jccs.200000052.
V. Naddaka, G. Davidi, E. Klopfer, O. Arad and J. Kaspi, Processes for Preparing 7-Hydroxy-3,4-dihydro-2(1H)-quinolinone and The Use in Aripiprazole Preparation Thereof, US patent 20060079690A1 (2006).
H. Yamashita, J. Matsubara, K. Oshima, H. Kuroda, N. Ito, S. Miyamura, S. Shimizu, T. Tanaka and H. Takahashi, Piperazine-Substituted Benzothiophenes for Treatment of Mental Disorders, WO Patent 2006112464 (2006).