pyridine ring), 9.09 (1H, d, J 2.3, pyridine ring), 10.62 (1H, br s,
NHCH2CH2CH3); dC(100 MHz, CDCl3) 12.1 (CH3), 22.9 (CH2),
43.8 (CH2), 113.7 (C), 121.8 (CH), 122.8 (CH), 130.6 (CH), 134.4
(C), 137.9 (CH), 147.4 (CH), 147.6 (CH), 155.4 (C), 159.6 (C);
m/z (EI) 258 (M+, 20%), 229 (100), 183 (40).
Ryabukhin, A. S. Plaskon, D. M. Volochnyuk and A. A. Tolmachev,
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5-Nitro-3-phenyl-2-(propylamino)pyridine (9k). Yellow oil
(Found: C, 65.47; H, 5.82; N, 16.21. C14H15N3O2 requires C,
65.35; H, 5.88; N, 16.33%). lmax(MeCN)/nm 371 (e/dm3 mol-1
cm-1 16 300); nmax(neat)/cm-1. dH(400 MHz, CDCl3) 0.93 (3H, t, J
7.4, NHCH2CH2CH3), 1.61 (2H, tq, J 7.0, 7.4, NHCH2CH2CH3),
3.49 (2H, dt, J 7.0, 7.0, NHCH2CH2CH3), 5.2–5.4 (1H, br t,
NHCH2CH2CH3), 7.39–7.46 (2H, m, benzene ring), 7.48–7.52
(3H, m, benzene ring), 8.02 (1H, d, J 2.4, pyridine ring), 9.04
(1H, d, J 2.4, pyridine ring); dC(100 MHz, CDCl3) 11.8 (CH3),
22.9 (CH2), 44.0 (CH2), 121.8 (C), 129.1 (CH), 129.4 (CH), 130.1
(CH), 132.0 (CH), 135.8 (C), 136.0 (C), 146.1 (CH), 159.1 (C);
m/z (EI) 257 (M+, 60%), 228 (100), 182 (74).
3-Benzoyl-5-nitro-2-(propylamino)pyridine (9m). White solid
(Found: C, 63.27; H, 5.46; N, 14.53. C15H15N3O3 requires C,
63.15; H, 5.30; N, 14.73%.); mp 120–121 ◦C. lmax(MeCN)/nm
358 (e/dm3 mol-1 cm-1 19 669); nmax(neat)/cm-1 3278 (NH), 1637
14 J. Reisch, L. Mester and S. M. El-Moghazy Aly, J. Chem. Soc. Perkin
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Trans. 1, 1983, 33, 219–223.
(C O), 1541, 1315 (NO2); dH(400 MHz, CDCl3) 1.05 (3H, t, J 7.4,
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NHCH2CH2CH3), 1.76 (2H, tq, J 6.8, 7.4, NHCH2CH2CH3),
3.68 (2H, dt, J 6.8, 6.8, NHCH2CH2CH3), 7.51–7.57 (2H, m,
benzene ring), 7.59–7.64 (3H, m, benzene rimg), 8.57 (1H, d, J 2.7,
pyridine ring), 9.19 (1H, d, J 2.7, pyridine ring), 9.5–9.7 (1H, br t,
NHCH2CH2CH3); dC(100 MHz, CDCl3) 11.9 (CH3), 22.8 (CH2),
43,8 (CH2), 112.3 (C), 129.2 (CH), 129.4 (CH), 132.8 (CH), 133.4
(C), 138.3 (C), 139.0 (CH), 151.3 (CH), 161.0 (C), 196.2 (C).
16 S. Nagato, K. Ueno, K. Kawano, Y. Norimine, K. Ito, T. Hanada, M.
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Acknowledgements
The authors thank Dr. K. Tahara (Osaka University) for his help
with single-crystal X-ray analysis.
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