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N. Chapman et al.
LETTER
(13) Ravi Kanth, S.; Venkat Reddy, G.; Rama Rao, V. V. V. N.
S.; Maitraie, D.; Narsaiah, B.; Shanthan Rao, P. Synth.
Commun. 2002, 32, 2849.
(14) Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J.
Tetrahedron 2001, 57, 9225.
References and Notes
(1) Knifton, J. F. J. Org. Chem. 1976, 41, 1200.
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1975, 26, 2163.
(3) Love, C.; McQuillin, F. J. J. Chem. Soc., Perkin Trans. 1
1973, 2509.
(15) Each isomer was separated and characterised by 1H NMR
and 13C NMR spectroscopy. For each isomer, an NOE was
observed between the NH2 and the aromatic proton.
(16) The conversion of 2-[(E)-2-(4-pyridinyl)ethenyl]aniline to
the 2-[2-(4-pyridinyl)ethyl]aniline required microwave
conditions of 180 °C, 120 min in EtOH.
(4) Onopchenko, A.; Sabourin, E. T.; Selwitz, C. M. J. Org.
Chem. 1979, 44, 1233.
(5) (a) Secrist, J. A. III; Logue, M. W. J. Org. Chem. 1972, 37,
335. (b) Rogers, M. E.; Averill, B. A. J. Org. Chem. 1986,
51, 3308. (c) Nakano, M.; Sato, Y. J. Org. Chem. 1987, 52,
1844. (d) Lee, M.; Lown, J. W. J. Org. Chem. 1987, 52,
5717. (e) Manabe, K.; Okamura, K.; Date, T.; Koga, K. J.
Org. Chem. 1993, 58, 6692. (f) Sleath, P. R.; Noar, J. B.;
Eberlein, G. A.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107,
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Choudary, B. M. Tetrahedron Lett. 1989, 30, 251.
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409. (c) Wetherill, R. B.; Brown, H. C.; Sivasankaran, K. J.
Am. Chem. Soc. 1962, 84, 2828.
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91, 3544. (c) Doxsee, K. M.; Feigel, M.; Stewart, K. D.;
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1987, 109, 3098. (d) Schiemann, G.; Pillarsky, R. Chem.
Ber. 1929, 62, 3035.
(17) 3-(Ethyloxy)-4-nitroaniline.
Synthesised using heating time of 3 min. 1H NMR [400
MHz, (CD3)2SO]: d = 1.35 (t, J = 8 Hz, 3 H, CH3), 4.05 (q,
J = 8 Hz, 2 H, CH2), 6.18 (d, J = 8 Hz, 1 H, ArH), 6.24 (s, 1
H, ArH), 6.53 (br s, 2 H, NH2), 7.78 (d, J = 8 Hz, 1 H, ArH),
7.71 (d, J = 8 Hz, ArH). 13C NMR [75 MHz, (CD3)2SO]:
d = 14.8, 64.5, 96.9, 105.9, 127.2, 129.3, 156.3, 156.5. MS
(EI, 70 eV): m/z (%) = 182.97 (100). HRMS-FAB: m/z calcd
for C8H10N2O3 [M + H]+: 183.0770; found: 183.0775.
2-(Ethyloxy)-4-nitroaniline.
Synthesised using heating time of 3 min. 1H NMR [400
MHz, (CD3)2SO]: d = 1.37 (t, J = 8 Hz, 3 H, CH3), 4.10 (q,
J = 8 Hz, 2 H, CH2), 6.40 (br s, 2H, NH2), 6.64 (d, J = 8 Hz,
1 H, ArH), 7.54 (s, 1 H, ArH), 7.71 (d, J = 8 Hz, ArH). 13
NMR [75 MHz, (CD3)2SO]: d = 14.5, 63.9, 106.3, 110.8,
119.6, 135.4, 143.6, 146.1. MS (EI, 70 eV): m/z
C
(%) = 182.85 (100). HRMS-FAB: m/z calcd for C8H10N2O3
[M + H]+: 183.0770; found: 183.0775.
2-[(E)-2-(4-pyridinyl)ethenyl]aniline.
Synthesised using heating time of 90 min. 1H NMR [400
MHz, (CD3)2SO]: d = 5.51 (s, 2 H, NH2), 6.55 (t, J = 4 Hz, 1
H, ArH), 6.65 (d, J = 8 Hz, 1 H, ArH), 6.96 (d, J = 16 Hz, 1
H, CH), 7.01 (m, 1 H, ArH), 7.47 (d, J = 8 Hz, 1 H, ArH),
7.57 (br d, J = 4 Hz, 2 H, ArH), 7.67 (d, J = 16 Hz, 1 H, CH),
8.51 (br s, 2 H, ArH). 13C NMR (75 MHz, CDCl3):
d = 115.7, 116.6, 119.4, 120.61, 123.7, 125.7, 128.8, 129.5,
145.1, 146.3, 149.2. MS (EI, 70 eV): m/z (%) = 197.0 (100).
HRMS-FAB: m/z calcd for C13H13N2 [M + H]+: 197.1083;
found: 197.1079.
(8) (a) Wentland, M. P.; Kullnig, R. K.; Tham, F. S. J. Org.
Chem. 1991, 56, 4706. (b) Mahood, S. A.; Schaffner, P. V.
L. Org. Synth,. Coll. Vol. II 1943, 160. (c) Fox, B. A.;
Threlfall, T. L. Org. Synth., Coll. Vol. V 1973, 346.
(9) Subba Rao, N. V.; Ratnam, C. V. Proc. Indian Acad. Sci.,
Sect. A 1956, 44, 331.
(10) (a) Linstead, R. P.; Braude, E. A.; Wooldridge, K. R. H. J.
Chem. Soc. 1954, 3586. (b) Entwistle, I. D.; Johnstone, R.
A. W.; Povall, T. J. J. Chem. Soc., Perkin Trans. 1 1975,
1300. (c) Yeh, M.; Tang, F.; Chen, S.; Liu, W.; Lin, L. J.
Org. Chem. 1994, 59, 754.
(11) (a) Frisch, K. C.; Taylor Bogert, M. J. Org. Chem. 1943, 8,
331. (b) Lyli, R. E.; Lamattina, J. L. Synthesis 1974, 726.
(c) Theodoridis, G.; Manfredi, M. C.; Krebs, J. D.
Tetrahedron Lett. 1990, 31, 6141.
(12) (a) Wong, J. C.; Wen-Ben, Y.; Chung-Ming, S. Synlett 2003,
1688. (b) Bendale, P. M.; Chung-Ming, S. J. Comb. Chem.
2002, 4, 359. (c) Kamal, A.; Srinivasa Reddy, K.; Rajendra
Prasad, B.; Hari Babu, A.; Venkata Ramana, A. Tetrahedron
Lett. 2004, 45, 6517.
1H-Indazol-6-amine
Synthesised using heating time of 15 min. 1H NMR [400
MHz, (CD3)2SO]: d = 5.18 (s, 2 H, NH2), 6.48 (dd, J = 8, 4
Hz, 1 H, ArH), 6.50 (s, 1 H, CH), 7.35 (d, J = 8 Hz, 1 H,
ArH), 7.71 (s, 1 H, ArH) 12.3 (s, NH). 13C NMR (75 MHz,
CDCl3): d = 89.6, 111.5, 114.7, 119.7, 132.3, 141.1, 146.8.
MS (EI, 70 eV): m/z (%) = 134.02 [M + H]+ (100). HRMS-
FAB: m/z calcd for C7H7N3 [M + H]+: 134.0717; found:
134.0718.
Synlett 2006, No. 7, 1043–1046 © Thieme Stuttgart · New York