LETTER
2-(3-Acetylphenylamino)benzaldehyde (5d)
Synthesis of 2-(N-Arylamino)benzaldehydes
2131
(100 MHz, CDC13): δ = 189.84, 150.15, 137.21, 136.25,
135.42, 135.02, 130.16, 129.35, 128.11, 126.65, 124.83,
123.13, 118.42, 115.25, 108.19, 21.06 ppm. MS (EI): m/z
(%) = 261 (100) [M+], 232 (85), 217 (53). Anal. Calcd for
C18H15NO: C, 82.73; H, 5.79; N, 5.36. Found: C, 82.85; H,
5.61; N, 5.24.
1H NMR (400 MHz, CDC13): δ = 10.12 (br s, 1 H, NH), 9.93
(s, 1 H, CHO), 7.89 (d, J = 2.40 Hz, 1 H), 7.71–7.73 (m, 1
H), 7.62 (dd, J1 = 7.60 Hz, J2 = 1.80 Hz, 1 H), 7.41–7.49 (m,
3 H), 7.27 (t, J = 8.40 Hz, 1 H), 6.91 (t, J = 7.40 Hz, 1 H),
2.63 (s, 3 H, CH3) ppm. 13C NMR (100 MHz, CDC13): δ =
197.21. 194.44, 147.04, 140.34, 138.44, 136.76, 135.74,
129.72, 127.24, 124.08, 122.10, 119.74, 117.91, 112.85,
26.79 ppm. MS (EI): m/z (%) = 239 (100) [M+], 210 (39),
196 (32), 168 (55), 167 (44). Anal. Calcd for C15H13NO2: C,
75.30; H, 5.48; N, 5.85. Found: C, 75.41; H, 5.35; N, 5.69.
2-(4-Chlorophenylamino)-3-methoxybenzaldehyde (5e)
1H NMR (400 MHz, CDC13): δ = 9.99 (s, 1 H, CHO), 8.77
(br s, 1 H, NH), 7.34 (dd, J1 = 7.20 Hz, J = 2.40 Hz, 1 H),
7.18 (d, J = 8.80 Hz, 2 H), 7.11–7.13 (m, 2 H), 6.82 (d, J =
8.80 Hz, 2 H), 3.77 (s, 3 H, OCH3) ppm. MS (EI): m/z (%) =
263 (34), 261 (100) [M+], 234 (26), 232 (76) 183 (38). Anal.
Calcd for C14H12ClNO: C, 64.25; H, 4.62; N, 5.35. Found: C,
64.30; H, 4.53; N, 5.24.
2-(4-Chlorophenylamino)naphthalene-1-carbaldehyde
(5h)
1H NMR (400 MHz, CDC13): δ = 11.57 (br s, 1 H, NH),
10.93 (s, 1 H, CHO), 8.36 (d, J = 6.80 Hz, 1 H), 7.79 (d, J =
9.20 Hz, 1 H), 7.72 (d, J = 8.0 Hz, 1 H), 7.58 (t, J = 7.20 Hz,
1 H), 7.24–7.39 (m, 6 H) ppm. 13C NMR (100 MHz,
CDC13): δ = 190.22, 149.11, 137.71, 137.38, 134.84,
130.58, 129.67, 129.40, 129.08, 126.94, 125.61, 123.49,
118.65, 114.84, 108.84 ppm. MS (EI): m/z (%) = 283 (34),
281 (100) [M+], 252 (46), 217 (98). Anal. Calcd for
C14H12ClNO: C, 72.47; H, 4.29; N, 4.97. Found: C, 72.29; H,
4.38; N, 4.80.
N-Phenyl 4-Methylaniline (8)
2-(4-Methylphenylamino)-5-bromobenzaldehyde (5f)
1H NMR (400 MHz, CDC13): δ = 9.91 (br s, 1 H, NH), 9.84
(s, 1 H, CHO), 7.66 (d, J = 2.40 Hz, 1 H), 7.39 (dd, J1 = 8.80
Hz, J2 = 2.20 Hz, 1 H), 7.22 (d, J = 8.0 Hz, 2 H), 7.16 (d, J =
8.40 Hz, 2 H), 7.04 (d, J = 8.80 Hz, 1 H), 2.39 (s, 3 H, CH3)
ppm. 13C NMR (100 MHz, CDC13): δ = 192.90, 147.33,
138.15, 138.13, 136.35, 134.91, 130.19, 123.62, 120.30,
114.97, 107.62, 21.04 ppm. MS (EI): m/z (%) = 291 (96),
289 (99) [M+], 262 (69), 260 (73), 167 (34). Anal. Calcd for
C14H12BrNO: C, 57.95; H, 4.17; N, 4.83. Found: C, 57.77; H,
4.10; N, 4.91.
1H NMR (400 MHz, CDC13): δ = 7.26–7.31 (m, 2 H), 7.14
(d, J = 8.0 Hz, 2 H), 7.04–7.07 (m, 4 H), 6.93 (t, J = 7.40 Hz,
1 H), 5.66 (br s, 1 H, NH), 2.36 (s, 3 H, CH3) ppm. 13C NMR
(100 MHz, CDC13): δ = 134.94, 140.28, 131.01, 129.92,
129.37, 120.38, 118.96, 116.93, 20.76 ppm.
(13) Munro, S. L. A.; Craik, D. J. Magn. Reson. Chem. 1994, 32,
335.
(14) (a) Bayles, R.; Johnson, M. C.; Maisey, R. F.; Turner, R. W.
Synthesis 1977, 33. (b) Mizuno, M.; Yamano, M. Org.
Synth. 2007, 84, 325. (c) Arava, V. R.; Bandatmakuru, S. R.
Synthesis 2013, 45, 1039. (d) Acemoglu, M.; Allmendinger,
T.; Calienni, J.; Cercus, J.; Loiseleur, O.; Sedelmeier, G. H.;
Xu, D. Tetrahedron 2004, 60, 11571. (e) Kam, L. E.;
Grimaud, L.; Oble, J. Angew. Chem. Int. Ed. 2005, 44, 7961.
(f) Yang, H.; Li, Z. B.; Shin, D. S.; Wang, L. Y.; Zhou, J. Z.;
Qiao, H. B.; Tian, X.; Ma, X. Y.; Zuo, H. Synlett 2010, 483.
2-(4-Methylphenylamino)naphthalene-1-carbaldehyde
(5g)
1H NMR (400 MHz, CDC13): δ = 11.60 (br s, 1 H, NH),
10.92 (s, 1 H, CHO), 8.37 (d, J = 8.40 Hz, 1 H), 7.74 (d, J =
9.20 Hz, 1 H), 7.70 (d, J = 8.0 Hz, 1 H), 7.56 (t, J = 7.20 Hz,
1 H), 7.21–7.35 (m, 6 H), 2.42 (s, 3 H, CH3) ppm. 13C NMR
© Georg Thieme Verlag Stuttgart · New York
Synlett 2013, 24, 2127–2131