Vol. 28, No. 10, 2017
do Amaral et al.
1877
9.0, H6), 8.39 (d, 1H, J 9.0, H5); 13C NMR (100 MHz,
DMSO-d6) d 149.2, 148.8, 148.3, 142.8, 140.2, 130.9,
124.1, 123.9; DEPT-135 (100 MHz, DMSO-d6) d 148.8,
130.9, 124.1, 123.9; MS 209.1 + 211.1.
Acknowledgments
The authors would like to thank INCT-INOFAR (BR,
573.564/2008-6 and E-26/170.020/2008), CAPES/PSDE
(BEX 4188/14-4), ICEPHA-Grants, DFG LA 1453/2-1 and
Prof Arthur E. Kümmerle (ICE-DQ-UFRRJ) and staff by
the NOE-dif experiment.
Procedure for the synthesis of N-(4-methoxybenzyl)-
7-nitroquinoxalin-2-amine (5)
20 mL of triethylamine (3 eq.) and 6.8 mL of
p-methoxybenzylamine (1.05 eq.) were added to a solution
of 2-chloro-7-nitroquinoxaline (4) (10.13 g, 48 mmol) in
ethanol (160 mL). The reaction mixture was refluxed for
3 h. The solution was evaporated and the solids were filtered
and washed with water to obtain an orange colored solid
(13.94 g). Yield 93%; mp 171-173 °C (lit. 167-169 ºC);13
ATR/FTIR n / cm-1 3389, 3077, 2928, 1615, 1538, 1509,
1338, 741; 1H NMR (200 MHz, DMSO-d6) d 8.50 (t, 2H,
J 6.0, NH and H3), 8.27 (d, 1H, J 2.0, H8), 8.05 (dd, 1H,
J 2.0, 9.0, H6), 7.96 (d, 1H, J 8.0, H5), 7.36 (d, 2H, J 8.0,
H3’), 6.91 (d, 2H, J 8.0, H4’), 4.56 (d, 2H, J 6.0, CH2),
3.73 (s, 3H, OCH3). 13C NMR (50 MHz, DMSO-d6)
d 158.4, 152.8, 147.5, 143.6, 141.4, 139.3, 130.4, 129.9,
129.2, 120.9, 116.8, 113.8, 55.1, 43.3; DEPT-135 (50 MHz,
DMSO-d6) d 143.6, 129.9, 129.2, 120.9, 116.8, 113.8,
55.1, 43.3; ESI-MS 309.3; HPLC at 230 nm 96.7% and
at 254 nm 100%.
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Supplementary Information
Supplementary information (1H and 13C NMR,
DEPT-135, FTIR spectra and TLC-MS data) is available
11. Gabler, M.; Schubert-Zsilavecz, M.; Molecules 2011, 16, 10013.
12. Fox, B. M.; Sugimoto, K.; Lio, K.; Yoshida, A.; Zhang, J.; Li,
K.; Hao, X.; Labelle, M.; Smith, M.; Rubenstein, S. M.;Ye, G.;