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Organic & Biomolecular Chemistry
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Journal Name
ARTICLE
4-chloro-N-(quinolin-2-yl)benzamide (4h):24
J. Org. Chem., 2016, 81, 7256; (d) M.DMOaI:j1e0k.1,0A3V.9i/eJDw. 0WAOrtaiBcn0le0gO5en6llii3nnKe,
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-F. Wu, ChemSusChem., 2016, 9, 1; (f) K. Wang, L. G. Meng, L.
Wang, J. Org. Chem., 2016, 81, 7080; (g) A. K. Yadav, L. D. S.
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12886; (i) J. C. Tellis, D. N. Primer, G. A. Molander, Science,
2014, 345, 433.
(a) R. Zhao, Y. Yao, D. Zhu, D. Chang, Y. Liu, L. Shi, Org. Lett.,
2018, 20, 1228; (b) H. Takenaka, Y. Masuhara, K. Narita, T.
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Wang, B. Huang, C. Shi, C. Yang, W. Xia, J. Org. Chem., 2018,
83, 9696; (d) H. G. Yayla, H. Wang, K. T. Tarantino, H. S. Orbe,
R. R. Knowles, J. Am. Chem. Soc., 2016, 138, 10794.
Y. Peng, C. T. Feng, Y-Q. Li, F-X. Chen, K. Xu, Org. Biomol.
Chem., 2019, 17, 6570.
Isolated as White solid in Hexane/EtOAc (92/8), 78% yield, 110
mg. 1H NMR (500 MHz, CDCl3) δ 8.88 (br, 1H), 8.56 (d, J = 6.5 Hz,
1H), 8.26 (d, J = 9.0 Hz, 1H), 7.95 (d, J = 8.0 Hz, 2H), 7.84 (t, J =
8.0 Hz, 2H), 7.71 (t, J = 7.5 Hz, 1H), 7.50 (t, J = 8.5 Hz, 3H). 13C{1H}
NMR (125 MHz, CDCl3) δ 165.6, 151.1, 146.7, 138.9, 138.8,
132.6, 130.2, 129.1, 128.8, 127.7, 127.2, 126.5, 125.4, 114.6.
7
2-methyl-N-(6-methylquinolin-2-yl)benzamide (4i):
New, Isolated as White solid in Hexane/EtOAc (90/10), 70%
o
1
yield, 97 mg. Rf = 0.72 (30% EtOAc/Hexane), mp 80-82 C. H
NMR (500 MHz, CDCl3) δ 8.56 (s, 1H), 8.55 (s, 1H), 8.18 (d, J =
9.0 Hz, 1H), 7.74 (d, J = 8.5 Hz, 1H), 7.62 (d, J = 8.5 Hz, 2H), 7.54
(d, J = 8.5 Hz, 1H), 7.41 (t, J = 7.5 Hz, 1H), 7.32 (d, J = 7.5 Hz, 2H),
2.58 (s, 3H), 2.55 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 168.5,
150.5, 145.0, 138.1, 136.8, 135.8, 135.1, 132.3, 131.5, 130.6,
127.0, 126.9, 126.6, 126.5, 125.9, 114.3, 21.7, 20.2. HRMS (ESI,
m/z) calcd. for C10H17O2 [M+Na]+ 299.1155, found 299.1150.
8
9
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H. Wang, RSC Adv., 2015, 5, 100102; (d) S. Yang, H. Yan, X. Ren,
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10 P. Chauhan, Ritu, Preeti, S. Kumar, N. Jain, Eur. J. Org. Chem.,
2019, 4334.
11 (a) A. Ashkenazi, X. Du, J. Qing, US Patent, 9358250 B2, 2016;
(b) B. Kelly, M. McMullan, J. E. Ortega, J. J. Meana, L. F.
Callado, I. Rozas, J. Med. Chem., 2015, 58, 963.
Conflicts of interest
There are no conflicts to declare.
12 T. Lazarides, T. McCormick, P. Du, G. Luo, B. Lindley, R.
Eisenberg, J. Am. Chem. Soc., 2009, 131, 9192.
13 W. –L. Lel, B. Yang, Q. –B. Zhang, P. –F. Yuan, L. –Z. Wu, Q. Liu,
Green Chem., 2018, 20, 5479.
Acknowledgements
Ritu thanks DST-INSPIRE for her graduate fellowship. The
authors thank IIT Delhi for funding the FIRP project no.
MI01692, and DST-FIST for funding the ESI-HRMS facility at IIT
Delhi.
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