Molecules 2017, 22, 1709
7 of 12
1
1089, 1047, 916, 876, 806, 786, 757, 725; H-NMR (DMSO-d6),
δ
: 13.47 (s, 1H), 10.83 (s, 1H), 8.33 (d,
1H, J = 8.6 Hz), 8.05–8.10 (m, 1H), 7.95 (d, 1H, J = 2.6 Hz), 7.93 (d, 1H, J = 8.2 Hz), 7.68 (ddd, 1H,
J = 8.2, J = 6.9, J = 1.3 Hz), 7.65 (d, 1H, J = 8.9 Hz), 7.60 (ddd, 1H, J = 8.3, J = 7.0, J = 1.2 Hz), 7.51
(d, 1H, J = 8.9 Hz), 7.42 (dd, 1H, J = 8.7, J = 2.5 Hz); 13C-NMR (DMSO-d6),
δ: 168.70, 158.81, 136.15,
135.64, 131.69, 130.92, 129.17, 127.67, 127.61, 127.40, 127.38, 126.03, 124.71, 123.48, 123.13, 118.58, 108.25;
HR-MS: [M − H]+ calculated 330.00831 m/z, found 330.00986 m/z.
◦
N-(2,6-Dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide (11). Yield 59%; m.p. 199–202 C; HPLC
purity 98.82%; IR (cm−1): 3309, 1635, 1616, 1596, 1568, 1529, 1499, 1448, 1435, 1383, 1331, 1283, 1252,
1
1209, 944, 796, 766, 721, 701; H-NMR (DMSO-d6),
δ: 13.85 (s, 1H), 10.76 (s, 1H), 8.28–8.33 (m, 1H),
8.11 (d, 1H, J = 8.9 Hz), 7.93 (d, 1H, J = 8.2 Hz), 7.69 (ddd, 1H, J = 8.1, J = 6.9, J = 1.2 Hz), 7.65 (d, 2H,
J = 8.2 Hz), 7.60 (ddd, 1H, J = 8.1, J = 7.0, J = 1.0 Hz), 7.50 (d, 1H, J = 8.6 Hz), 7.47 (t, 1H, J = 8.2 Hz);
13C-NMR (DMSO-d6),
124.56, 123.07, 122.72, 118.23, 106.37; HR-MS: [M
δ: 169.90, 160.22, 136.15, 134.14, 132.10, 130.02, 129.37, 128.69, 127.58, 126.12,
−
H]+ calculated 330.00831 m/z, found 330.00943 m/z.
◦
N-(3,4-Dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide (12). Yield 84%; m.p. 195–197 C; HPLC
purity 99.14%; IR (cm−1): 3429, 1628, 1601, 1584, 1574, 1527, 1504, 1467, 1390, 1320, 1298, 1274, 1247,
1210, 1144, 1127, 1088, 1026, 939, 871, 797, 785, 759, 729; 1H-NMR (DMSO-d6),
δ: 13.85 (s, 1H), 10.76 (s,
1H), 8.28–8.33 (m, 1H), 8.11 (d, 1H, J = 8.9 Hz), 7.93 (d, 1H, J = 8.2 Hz), 7.69 (ddd, 1H, J = 8.1, J = 6.9,
J = 1.2 Hz), 7.65 (d, 2H, J = 8.2 Hz), 7.60 (ddd, 1H, J = 8.1, J = 7.0, J = 1.0 Hz), 7.50 (d, 1H, J = 8.6 Hz),
7.47 (t, 1H, J = 8.2 Hz); 13C-NMR (DMSO-d6),
δ: 169.56, 159.90, 137.90, 136.06, 130.86, 130.52, 129.28,
127.47, 126.21, 126.00, 124.56, 123.09, 123.00, 122.94, 121.68, 117.99, 107.42; HR-MS: [M
330.00831 m/z, found 330.00970 m/z.
−
H]+ calculated
◦
N-(3,5-Dichlorophenyl)-1-hydroxynaphthalene-2-carboxamide (13). Yield 80%; m.p. 190–194 C; HPLC
purity 99.09%; IR (cm−1): 3431, 1626, 1585, 1568, 1526, 1504, 1443, 1407, 1387, 1300, 1267, 1204, 1144,
1
1086, 882, 823, 787, 755, 723; H-NMR (DMSO-d6),
δ
: 13.48 (br. s, 1H), 10.61 (s, 1H), 8.31 (d, 1H,
J = 8.2 Hz), 8.04 (d, 1H, J = 8.9 Hz), 7.91 (d, 1H, J = 8.2 Hz), 7.88 (d, 2H, J = 1.6 Hz), 7.68 (ddd, 1H,
J = 8.1, J = 7.0, J = 1.3 Hz), 7.58 (ddd, 1H, J = 8.1, J = 7.0, J = 1.0 Hz), 7.48 (d, 1H, J = 8.9 Hz), 7.39 (t,
1H, J = 1.8 Hz); 13C-NMR (DMSO-d6),
δ: 169.69, 159.91, 140.23, 136.12, 133.92, 129.37, 127.50, 126.06,
124.56, 123.70, 123.13, 122.94, 119.74, 118.08, 107.45; HR-MS: [M
330.00958 m/z.
−
H]+ calculated 330.00831 m/z, found
1-Hydroxy-N-(2,4,5-trichlorophenyl)naphthalene-2-carboxamide (14). Yield 77%; m.p. 211–215 ◦C; HPLC
purity 98.56%; IR (cm−1): 3422, 1630, 1574, 1514, 1501, 1470, 1446, 1392, 1367, 1320, 1287, 1269, 1242,
1205, 1146, 1088, 1068, 947, 884, 829, 876, 797, 785, 760, 715, 678; 1H-NMR (DMSO-d6),
δ: 13.39 (br. s,
1H), 10.90 (s, 1H), 8.33 (d, 1H, J = 8.7 Hz), 8.18 (s, 1H), 8.06 (d, 1H, J = 8.7 Hz), 8.03 (s, 1H), 7.93 (d,
1H, J = 7.8 Hz), 7.68 (ddd, 1H, J = 8.0, J = 6.9, J = 1.4 Hz), 7.60 (ddd, 1H, J = 8.2, J = 6.9, J = 1.4 Hz),
7.51 (d, 1H, J = 8.7 Hz); 13C-NMR (DMSO-d6),
δ: 168.63, 158.72, 136.19, 134.59, 130.67, 130.05, 129.24,
129.10, 128.55, 128.33, 127.64, 126.09, 124.71, 123.52, 123.16, 118.68, 108.30; HR-MS: [M
363.96934 m/z, found 363.97119 m/z.
−
H]+ calculated
1-Hydroxy-N-(2,4,6-trichlorophenyl)naphthalene-2-carboxamide (15). Yield 75%; m.p. 214–216 ◦C; HPLC
purity 98.91%; IR (cm−1): 3303, 1631, 1616, 1597, 1556, 1524, 1500, 1468, 1445, 1407, 1385, 1320, 1278,
1241, 1211, 1189, 1154, 1142, 942, 851, 832, 796, 763, 713; 1H-NMR (DMSO-d6),
δ: 13.73 (br. s, 1H), 10.79
(s, 1H), 8.30 (d, 1H, J = 8.7 Hz), 8.09 (d, 1H, J = 9.2 Hz), 7.93 (d, 1H, J = 8.2 Hz), 7.89 (s, 2H), 7.70 (ddd,
1H, J = 8.2, J = 6.9, J = 1.4 Hz), 7.60 (ddd, 1H, J = 8.2, J = 7.1, J = 1.1 Hz), 7.50 (d, 1H, J = 9.2 Hz); 13C-NMR
(DMSO-d6), δ: 169.92, 160.22, 136.19, 134.96, 133.31, 131.54, 129.46, 128.50, 127.61, 126.18, 124.53, 123.09,
122.68, 118.33, 106.27; HR-MS: [M − H]+ calculated 363.96934 m/z, found 363.97119 m/z.
1-Hydroxy-N-(3,4,5-trichlorophenyl)naphthalene-2-carboxamide (16). Yield 71%; m.p. 245–248 ◦C; HPLC
purity 99.28%; IR (cm−1): 3430, 1627, 1598, 1575, 1515, 1501, 1467, 1432, 1380, 1356, 1309, 1287, 1267,
1244, 1205, 1150, 1076, 959, 882, 870, 822, 797, 787, 757, 723, 682; 1H-NMR (DMSO-d6),
δ: 13.41 (br. s,
1H), 10.64 (s, 1H), 8.29 (d, 1H, J = 8.2 Hz), 8.08 (s, 2H), 8.02 (d, 1H, J = 9.2 Hz), 7.90 (d, 1H, J = 8.2 Hz),