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K. A. Reynolds et al.
PAPER
The 1H NMR spectrum was consistent with previously reported da-
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References
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2-(2-Nitrophenyl)quinoline (15)
Following the general procedure using aniline (0.98 mL, 10.74
mmol) and trans-2-nitrocinnamaldehyde (3.80 g, 21.47 mmol) gave
a brown solid; yield: 3 mg (<1%); mp 116–117 °C (Lit.22 118–119
°C)
1H NMR (400 MHz, CDCl3): d = 7.53 (d, J = 8.4 Hz, 1 H, H3),
7.55–7.61 (m, 2 H, H6, H5¢), 7.70–7.76 (m, 3 H, H7, H4¢, H6¢), 7.86
(d, J = 6.8 Hz, 1 H, H8), 7.98 (d, J = 9.2 Hz, 1 H, H3¢), 8.09 (d,
J = 9.6 Hz, 1 H, H5), 8.23 (d, J = 8.4 Hz, 1 H, H4).
13C NMR (125 MHz, CDCl3): d = 120.5, 124.5, 127.0, 127.2, 127.5,
129.3, 129.7, 130.0, 131.6, 132.6, 135.9, 136.8, 147.9, 155.6.
MS (ESI) m/z (%) = 205.68 (100); 250.73 (30) [M + 1].
HRMS: m/z [M + H]+ calcd for C15H11N2O2: 251.0815; found:
251.0823.
(6) (a) O’Neill, P. M.; Storr, R. C.; Park, B. K. Tetrahedron
1998, 54, 4615. (b) Fotie, J. Anti-Infect. Agents Med. Chem.
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6-Methoxy-2-methylquinoline (20)
Following the general procedure using 4-methoxyaniline (0.94 mL,
8.12 mmol) and crotonaldehyde (1.35 mL, 16.24 mmol) gave a
brown solid; yield: 106 mg (8%); mp 60–62 °C (Lit.23 67–68 °C).
The 1H NMR spectrum was consistent with previously reported da-
(8) Wu, Y.; Liu, L.; Li, H.; Wang, D.; Chen, Y. J. Org. Chem.
ta.23,24
2006, 71, 6592.
(9) (a) Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006,
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1883, 2464.
2,8-Dimethylquinoline (21)
Following the general procedure using 2-methylaniline (0.49 mL,
4.66 mmol) and crotonaldehyde (0.77 mL, 9.33 mmol) gave a yel-
low oil; yield: 54 mg (7%).
The 1H NMR spectrum was consistent with previously reported da-
(11) Matsugi, M.; Tabusa, F.; Minamikawa, J.-I. Tetrahedron
Lett. 2000, 41, 8523.
ta.23
(12) Sivaprasad, G.; Rajesh, R.; Perumal, P. T. Tetrahedron Lett.
2-Methyl-6-nitroquinoline (22)
2006, 47, 1783.
Following the general procedure using 4-nitroaniline (0.5 g, 3.62
mmol) and crotonaldehyde (0.60 mL, 7.24 mmol) gave dark-green
crystals; yield: 154 mg (23%); mp 162–164 °C (Lit.25 165 °C).
(13) Li, X. G.; Cheng, X.; Zhou, Q. L. Synth. Commun. 2002, 32,
2477.
(14) (a) Sato, E. Chem. Pharm. Bull. 1990, 38, 1205. (b) Endo,
T.; Saeki, S.; Hamana, M. Chem. Pharm. Bull. 1981, 29,
3105.
The 1H NMR spectrum was consistent with previously reported da-
ta.25
(15) Calf, G. E.; Samuel, E. L. Aust. J. Chem. 1963, 16, 833.
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6-Bromo-2-methylquinoline (23)
Following the general procedure using 4-bromoaniline (0.5 g, 2.91
mmol) and crotonaldehyde (0.48 mL, 5.81 mmol) gave red-brown
crystals; yield: 48 mg (16%); mp 97–99 °C (Lit.26 95–96 °C).
(19) Crisp, G. T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279.
(20) Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353.
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2007, 63, 673.
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Chem. 2005, 70, 1222.
IR (KBr): 3048, 1488, 646 cm–1
1H NMR (400 MHz, CDCl3): d = 2.752 (s, 3 H, CH3), 7.319 (d,
J = 8.4 Hz, 1 H, H3), 7.754 (d, J = 2.0, 2.0 Hz, 1 H, H4), 7.917 (br
s, w ~7.0 Hz, 1 H, H5), 7.942 (d, J = 2.2 Hz, 1 H, H7), 7.981 (d,
J = 8.9 Hz, 1 H, H8)
13C NMR (100 MHz, CDCl3): d = 25.2, 119.4, 122.8, 127.5, 129.4,
130.2, 132.8, 135.2, 146.2, 159.4.
MS (ESI) m/z (%) = 223.73 (100) [M + H]+.
HRMS: m/z [M + H]+ calcd for C10H9Br1N1: 221.9912; found:
221.9902.
(25) Tahtaoui, C.; Guillier, F.; Klotz, P.; Galzi, J.-L.; Hibert, M.;
Ilien, B. J. Med. Chem. 2005, 48, 7847.
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Supporting Information for this article is available online at
Trans. 1 1975, 394.
Acknowledgment
K.A.R. gratefully acknowledges a scholarship from Griffith Uni-
versity.
Synthesis 2010, No. 21, 3645–3648 © Thieme Stuttgart · New York