586
M. WANG, Z. G. SONG, AND Y. LIANG
analysis with those reported for the authentic samples. Spectral data for some new
compounds are as follows.
N-((2-Chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)benzamide (4e).
White solid. Mp: 266–268 ꢀC. IR (KBr): v 3426, 3067, 1633, 1573, 1538, 1346,
1
1075, 822, 752, 711 cmꢂ1. H NMR (500 MHz, DMSO-d6): d 9.93 (s, 1H, OH),
9.01 (d, 1H, J ¼ 6.2 Hz, NH), 8.08 (d, 1H, J ¼ 8.6 Hz, ArH), 7.89 (d, 2H, J ¼ 7.3 Hz,
ArH), 7.82 (d, 1H, J ¼ 7.7 Hz, ArH), 7.78 (d, 1H, J ¼ 8.8 Hz, ArH), 7.52 (t, 1H,
J ¼ 7.3 Hz, ArH), 7.44–7.40 (m, 5H, ArH), 7.36 (d, 1H, J ¼ 5.0 Hz, CH), 7.30–7.22
(m, 3H, ArH), 7.19 (d, 1H, J ¼ 8.8 Hz, ArH). 13C NMR (125 MHz, DMSO-d6): d
165.4, 153.7, 138.8, 134.2, 132.9, 132.7, 131.1, 130.1, 129.4, 128.6, 128.5, 128.3,
128.1, 127.4, 126.6, 126.3, 122.8, 122.3, 118.6, 116.8, 48.6. Anal. calcd. for
C24H18NO2Cl: C, 74.32; H, 4.68; N, 3.61. Found: C, 74.41; H, 4.60; N, 3.55%.
N-((2,4-Dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)benzamide
(4g). White solid. Mp: 235–238 ꢀC. IR (KBr): v 3423, 3069, 1633, 1574, 1536, 1344,
1
1074, 819, 748, 709 cmꢂ1. H NMR (500 MHz, DMSO-d6): d 9.98 (s, 1H, OH), 9.17
(d, 1H, J ¼ 6.3 Hz, NH), 8.05 (d, 1H, J ¼ 8.6 Hz, ArH), 7.89 (d, 2H, J ¼ 7.2 Hz,
ArH), 7.82 (d, 1H, J ¼ 7.6 Hz, ArH), 7.78 (d, 1H, J ¼ 8.8 Hz, ArH), 7.57 (d, 1H,
J ¼ 2.1 Hz, ArH), 7.52–7.42 (m, 5H, ArH), 7.37 (dd, 1H, J ¼ 2.1, 6.3 Hz, CH),
7.30–7.27 (m, 2H, ArH), 7.18 (d, 1H, J ¼ 8.8 Hz, ArH). 13C NMR (125 MHz,
DMSO-d6): d 165.5, 153.8, 138.2, 134.1, 133.6, 132.7, 132.1, 131.4, 131.2,
129.6, 128.6, 128.3, 128.1, 127.5, 126.7, 126.5, 122.6, 122.4, 118.6, 116.1, 48.3. Anal.
calcd. for C24H17NO2Cl2: C, 68.26; H, 4.06; N, 3.32. Found: C, 68.34; H, 4.01; N,
3.34%.
N-(1-(2-Hydroxynaphthalen-1-yl)butyl)benzamide (4l). White solid. Mp:
240–242 ꢀC. IR (KBr): v 3415, 3221, 3204, 1632, 1575, 1528, 1342, 1074, 815, 747,
.
715 cmꢂ1 1H NMR (500 MHz, DMSO-d6): d 10.08 (s, 1H, OH), 8.60 (d, 1H,
J ¼ 6.3 Hz, NH), 8.22 (d, 1H, J ¼ 7.7 Hz, ArH), 7.81 (t, 3H, J ¼ 7.2 Hz, ArH), 7.71
(d, 1H, J ¼ 8.8 Hz, ArH), 7.53–7.44 (m, 4H, ArH), 7.31 (t, 1H, J ¼ 7.3 Hz, ArH),
7.20 (d, 1H, J ¼ 8.8 Hz, ArH), 6.04 (q, 1H, J ¼ 7.0 Hz, CH), 2.19–2.11 (m, 1H,
CH2), 1.92–1.85 (m, 1H, CH2), 1.51–1.41 (m, 1H, CH2), 1.33–1.23 (m, 1H, CH2),
0.93 (t, 3H, J ¼ 7.3 Hz, CH3). 13C NMR (125 MHz, DMSO-d6): d 165.2, 152.8,
134.7, 132.1, 131.0, 128.5, 128.4, 128.3, 128.2, 126.9, 126.2, 122.3, 119.8, 118.6,
118.5, 46.6, 36.0, 19.6, 13.8. Anal. calcd. for C21H21NO2: C, 78.97; H, 6.63; N,
4.39. Found: C, 78.88; H, 6.59; N, 4.42%.
ACKNOWLEDGMENT
This research work was financially supported by the Committee of Science and
Technology of Liaoning Province of China (No. 20091001).
REFERENCES
1. Shen, A. Y.; Tsai, C. T.; Chen, C. L. Synthesis and cardiovascular evaluation of
N-substituted 1-aminomethyl-2-naphthols. Eur. J. Med. Chem. 1999, 34, 877.