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New Journal of Chemistry
Page 7 of 11
Journal Name
MHz, CDCl3):
DOI: 10.1039/C5NJ02010G
ARTICLE
δ
(ppm) 169.2, 154.3, 147.1, 141.4, 130.0, 129.2, 128.5, 128.4, 128.3, 126.1, 124.9, 76.7-77.3 (t, CHCl3), 23.9; MS
127.9, 126.3, 125.7, 123.9, 76.7-77.3 (t, CHCl3), 61.7, 23.8, (APCI) m/z 324.38 (M+H)+.
15.7, 14.3; MS (APCI) m/z 230.11 (M+H)+.
tert-Butyl 2,4-dimethylquinoline-3-carboxylate (Entry 11,
1-(2-Methyl-4-phenylquinolin-3-yl)ethanone (Entry 6, Table Table 4): Yellow solid; mp: 109-110 °C; IR (KBr) νmax: 3418,
4)3f: Brown solid; mp: 100-103 °C, (lit3f 111-112 °C); IR (KBr) 2954, 1556, 1540, 1370, 1233, 1220, 1158, 1043, 761, 678 cm-
1
1
νmax: 3348, 3051, 1690, 1561, 1395, 1216, 1021, 714 cm-1; H 1; H NMR (400 MHz, CDCl3):
δ
(ppm) 7.82 (d, J = 7.8 Hz, 1H)
(ppm) 8.08 (d, J = 8.4 Hz, 1H), 7.72 (t, 7.56 (d, J = 7.2 Hz, 1H), 7.35 (d, J = 7.9 Hz, 1H), 7.26 (d, J = 8.0
J = 7.0 Hz, 1H), 7.62 (d, J = 8.2 Hz, 1H), 7.51 (s, 3H), 7.44 (t, J = Hz, 1H), 3.38 (s, 9H), 2.46 (s, 3H), 2.34 (s, 3H); 13C NMR (100
7.6, 1H), 7.36 (d, J = 3.3, 2H), 7.26 (s, CHCl3), 2.70 (s, 3H), 2.00 MHz, CDCl3): (ppm); 204.0, 160.0, 144.1, 138.5, 133.3, 131.6,
NMR (400 MHz, CDCl3):
δ
δ
(s, 3H); 13C NMR (100 MHz, CDCl3):
δ (ppm) 205.7, 153.6, 126.1, 126.0, 122.7, 119.6, 116.1, 81.3, 76.7-77.3 (t, CHCl3),
147.5, 143.9, 135.2, 134.8, 130.1, 130.0, 128.9, 128.8, 128.7, 31.8, 22.4, 15.6; MS (APCI) m/z 258.31 (M+H)+. HRMS (ESI) m/z
126.5, 126.1, 125.0, 76.7-77.3 (t, CHCl3), 31.9, 23.9; MS (APCI) calcd for C16H19NO2Na+ [M+Na+], 280.1308; Found 280.1310.
m/z 262.18 (M+H)+.
9-Phenyl-3,4-dihydroacridin-1(2H)-one (Entry 12, Table 4)3g:
Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate Brown solid; mp: 156-158 °C, (lit3g 159 °C); IR (KBr) νmax: 3439,
(Entry 7, Table 4)3f: Yellow solid; mp: 133-135 °C, (lit3f 133-135 3066, 2951, 2867, 1686, 1555, 1223, 1151, 755, 710 cm-1; H
1
°C); IR (KBr) νmax: 3445, 3060, 2951, 2925, 2853, 1731, 1604, NMR (400 MHz, CDCl3):
δ (ppm) 8.08 (d, J = 8.4 Hz, 1H), 7.76-
1581, 1482, 1435, 1382, 1343, 1309, 1279, 1221, 1162, 1126, 7.80 (m, 1H), 7.39-7.43 (m, 1H), 7.47-7.54(m, 4H), 7.19-7.21
1
1082, 1068, 950, 931 cm-1; H NMR (400 MHz, CDCl3):
8.01 (d, J = 8.9 Hz, 1H), 7.65 (dd, J = 2.2 Hz, 1H), 7.49-7.55 (m, 2.30 (m, 2H); 13C NMR (100 MHz, CDCl3):
4H), 7.34 (dd, J = 2.9 Hz, 2H), 7.26 (s, CHCl3), 3.58 (s, 3H), 2.75 MHz, CDCl3): (ppm) 198.1, 162.3, 151.5, 148.7, 137.7, 131.8,
(s, 3H); 13C NMR (100 MHz, CDCl3):
(ppm) 168.6, 154.9, 128.5, 128.3, 128.1, 128.0, 127.6, 127.5, 126.4, 123.8, 76.7-
δ
(ppm) (m, 2H), 3.39 (t, J = 6.1 Hz, 2H), 2.72 (t, J = 6.8 Hz, 2H), 2.24-
(ppm) 13C NMR (100
δ
δ
δ
146.1, 145.6, 134.9, 132.4, 131.3, 130.5, 129.1, 128.9, 128.5, 77.3 (t, CHCl3), 40.7, 34.7, 21.4; MS (APCI) m/z 274.46 (M+H)+.
128.1, 125.9, 125.3, 76.7-77.3 (t, CHCl3), 52.3, 23.7; MS (APCI) 3-Methyl-9-phenyl-3,4-dihydroacridin-1(2H)-one (Entry 13,
m/z 312.76 (M+H)+.
Table 4): Yellow solid; mp: 183-185 °C; IR (KBr) νmax: 3425,
1
(6-Chloro-2-methyl-4-phenylquinolin-3-
yl)(phenyl)methanone (Entry 8, Table 4)4k: Yellow solid; mp: (400 MHz, CDCl3):
3051, 2955, 1690, 1555, 1211, 1040, 775, 703 cm-1; H NMR
δ (ppm) 8.06 (d, J = 8.4 Hz, 1H), 7.78 (t, J =
209-211 °C, (lit4k 209-211 °C); IR (KBr) νmax: 3456, 3058, 2958, 6.7 Hz, 1H), 7.38-7.53 (m, 5H), 7.16-7.19 (m, 2H), 3.43-3.49 (m,
2925, 2854, 1671, 1596, 1578, 1481, 1447, 1379, 1341, 1315, 1H), 3.01-3.08 (m, 1H), 2.73-2.78 (m, 1H), 2.38-2.50 (m, 2H),
1275, 1230, 1130, 1076, 1042, 1011, 968, 906, 879, 832, 786, 1.21 (d, J = 6.3 Hz, 3H); 13C NMR (100 MHz, CDCl3):
δ (ppm)
198.0, 161.7, 151.3, 148.8, 137.6, 131.8, 128.5, 128.3, 128.2,
763, 723, 699, 601,513 cm-1; 1H NMR (400 MHz, CDCl3):
δ
(ppm) 8.09 (d, J = 8.9 Hz, 1H), 7.70 (dd, J = 2.2 Hz, 1H), 7.57- 128.1, 128.07, 128.01, 127.6, 127.5, 126.5, 123.2, 76.7-77.3 (t,
7.61 (m, 3H), 7.48 (t, J = 7.3 Hz, 1H), 7.28-7.33 (m, 5H), 7.28 (s, CHCl3), 48.7, 42.9, 28.6, 21.3; MS (APCI) m/z 288.33 (M+H)+.
CHCl3), 7.20 (s, 2H), 2.63 (s, 3H); 13C NMR (100 MHz, CDCl3):
δ
(ppm) 197.4, 155.1, 146.2, 144.8, 136.9, 134.1, 133.7, 133.3, Found 310.1205.
HRMS (ESI) m/z calcd for C20H17NONa+ [M+Na+], 310.1202;
132.5, 131.0, 130.6, 129.9, 129.2, 128.6, 128.5, 128.3, 126.2, 3,3-Dimethyl-9-phenyl-3,4-dihydroacridin-1(2H)-one (Entry
125.0, 76.7-77.3 (t, CHCl3), 24.0; MS (APCI) m/z 358.83 (M+H)+. 14, Table 4)4j: Yellow solid; mp: 239-241 °C, (lit4j 240-241 °C);
1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)ethanone (Entry IR (KBr) νmax: 3352, 3065, 2931, 1943, 1688, 1552, 1372, 771,
9, Table 4)3g: Yellow solid; mp: 149-152 °C, (lit3g 157 °C); IR 691 cm-1; H NMR (400 MHz, CDCl3):
1
δ (ppm) 8.09 (d, J = 8.4
(KBr) νmax: 3460, 3051, 2926, 2855, 1918, 1702, 1567, 1479, Hz, 1H), 7.62-7.80 (m, 1H), 7.49-7.54 (m, 4H), 7.40-7.44 (m,
1354, 1196, 1126, 1079, 1048, 962, 936, 877, 857, 832, 790, 1H), 7.19-7.21 (m, 2H), 3.29 (s, 2H), 2.59 (s, 2H), 1.18 (s, 6H);
767, 710, 690, 642, 621, 582, 536, 477 cm-1; 1H NMR (400 MHz, 13C NMR (100 MHz, CDCl3):
δ
(ppm) 198.0, 161.1, 151.0, 149.0,
(ppm) 8.02 (d, J = 8.9 Hz, 1H), 7.66 (d, J = 8.9 Hz, 1H), 137.6, 131.7, 128.5, 128.3, 128.1, 128.0, 127.6, 127.4, 126.5,
7.56 (d, J = 8.6 Hz, 4H), 7.35 (d, J = 3.4 Hz, 2H), 7.28 (s, CHCl3), 122.7, 76.7-77.3 (t, CHCl3), 54.2, 48.4, 32.3, 28.4; MS (APCI)
2.69 (s, 3H), 2.01 (s, 3H); 13C NMR (100 MHz, CDCL3): (ppm) m/z 302.29 (M+H)+.
CDCl3):
δ
δ
205.3, 154.0, 145.9, 143.1, 135.5, 134.5, 132.5, 131.0, 130.5, 3,9-Diphenyl-3,4-dihydroacridin-1(2H)-one (Entry 15, Table
129.9, 129.3, 129.0, 125.9, 124.9, 76.7-77.3 (t, CHCl3), 31.9, 4): Yellow solid; mp: 274 °C; IR (KBr) νmax: 3432, 3025, 1691,
23.8; MS (APCI) m/z 296.76 (M+H)+.
(2-Methyl-4-phenylquinolin-3-yl)(phenyl)methanone (Entry CDCl3):
10, Table 4)4k: Yellow solid; mp: 132-135 °C, (lit4k 133-134 °C); 7.57 (m, 4H), 7.28-7.47 (m, 6H), 7.22-7.25 (m, 2H), 3.55-3.76
IR (KBr) νmax: 3501, 3158, 2929, 2884, 1691, 1578, 1501, 1421, (m, 3H), 2.92-3.05 (m, 2H); 13C NMR (100 MHz, CDCl3):
(ppm)
1369, 1321, 1265, 1239, 1076, 1031, 945, 842, 783, 753, 690 197.2, 161.2, 151.6, 149.0, 142.8, 137.5, 131.9, 129.0, 128.3,
1551, 1488, 1381, 1215, 1048, 761 cm-1; 1H NMR (400 MHz,
δ
(ppm) 8.11 (d, J = 8.4 Hz, 1H), 7.89-7.83 (m, 1H), 7.51-
δ
1
cm-1; H NMR (400 MHz, CDCl3):
δ (ppm) 8.08 (d, J = 8.9 Hz, 128.2, 128.1, 128.0, 127.7, 127.6, 127.1, 126.7, 126.6, 123.1,
1H), 7.68 (dd, J = 2.2 Hz, J = 9.2 Hz, 1H), 7.56-7.60 (m, 3H), 7.46 76.7-77.3 (t, CHCl3), 47.8, 42.2, 39.0;; m/z 349.14 (M+H)+.
(t, J = 7.3 Hz, 1H), 7.26-7.32 (m, 5H), 7.19 (s, 3H), 2.62 (s, 3H); HRMS (ESI) m/z calcd for C25H19NONa+ [M+Na+], 372.1359;
13C NMR (100 MHz, CDCl3):
δ (ppm) 197.3, 155.0, 146.1, 144.7, Found 372.1360.
136.8, 134.0, 133.6, 133.2, 132.4, 131.0, 130.5, 129.9, 129.1, 9-Phenyl-2,3-Dihydro-1H-cyclopenta[b]quinoline (Entry 16,
Table 4)4j: Yellow solid; mp: 129-131 °C, (lit4j 129-130 °C); IR
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