Page 13 of 19
The Journal of Organic Chemistry
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(d, J = 7.7 Hz, 3H), 7.63ꢀ7.57 (m, 1H), 7.27 (d, J = 8.2 Hz, 2H), 4.07 (s, 3H), 3.69 (s, 3H), 2.43 (s, 3H). 13
C
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NMR (100 MHz, CDCl3): 194.0, 166.3, 165.2, 149.1, 148.3, 147.5, 145.6, 133.9, 132.2, 130.4, 129.7, 129.6,
129.5, 126.1, 124.6, 121.2, 53.3, 52.8, 21.8. IR (cmꢀ1): 3066, 3039, 2957, 2925, 2851, 1740, 1669, 1603,
1560, 1497, 1442, 1395, 1364, 1309, 1250, 1202, 1179, 1154, 1127, 1079, 985, 937, 830, 772, 742, 710, 612.
HRMS (ESI) m/z calcd for C21H18NO5+ (M+H)+: 364.1179, found 364.1179.
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Dimethyl 4ꢀ(3,4ꢀdimethylbenzoyl)quinolineꢀ2,3ꢀdicarboxylate (4c). CAS: 1374309ꢀ25ꢀ7. 57 mg, 50%, m. p.
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= 124ꢀ125oC, H NMR (400 MHz, CDCl3): 8.32 (d, J = 8.5 Hz, 1H), 7.88 (ddd, J = 8.4, 6.9, 1.3 Hz, 1H),
7.69 (dd, J = 8.4, 0.7 Hz, 1H), 7.65ꢀ7.56 (m, 2H), 7.46 (d, J = 7.6 Hz, 1H), 7.21 (d, J = 7.9 Hz, 1H), 4.08 (s,
3H), 3.70 (s, 3H), 2.34 (s, 3H), 2.29 (s, 3H). 13C NMR (100 MHz, CDCl3): 194.3, 166.3, 165.2, 149.1, 148.5,
147.5, 144.4, 137.5, 134.3, 132.2, 130.4, 130.1, 129.4, 127.4, 126.2, 124.7, 121.1, 53.3, 52.9, 20.2, 19.6. IR
(cmꢀ1): 3070, 3039, 2957, 2921, 2851, 1732, 1669, 1603, 1563, 1501, 1442, 1399, 1368, 1305, 1250, 1200,
1172, 1129, 1074, 1043, 998, 953, 867, 791, 769, 733, 706, 628, 595, 586. HRMS (ESI) m/z calcd for
+
C22H20NO5 (M+H)+: 378.1336, found 378.1335.
Dimethyl 4ꢀ(4ꢀmethoxybenzoyl)quinolineꢀ2,3ꢀdicarboxylate (4d). CAS: 1374309ꢀ23ꢀ5. 48 mg, 42%, m. p. =
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130ꢀ132oC, H NMR (400 MHz, CDCl3): 8.31 (d, J = 8.5 Hz, 1H), 7.94ꢀ7.84 (m, 1H), 7.76 (d, J = 7.4 Hz,
2H), 7.70 (d, J = 8.4 Hz, 1H), 7.61 (dd, J = 8.3, 7.0 Hz, 1H), 6.94 (d, J = 8.0 Hz, 2H), 4.07 (s, 3H), 3.87 (s,
3H), 3.70 (s, 3H). 13C NMR (100 MHz, CDCl3): 192.8, 166.2, 165.3, 164.5, 148.9, 148.2, 147.5, 132.2,
131.8, 130.4, 129.5, 126.1, 124.6, 121.3, 114.2, 55.5, 53.3, 52.8. IR (cmꢀ1): 3072, 3029, 2957, 2843, 1736,
1665, 1599, 1575, 1509, 1442, 1399, 1376, 1309, 1250, 1200, 1168, 1129, 1078, 1027, 980, 937, 839, 773,
+
636, 608. HRMS (ESI) m/z calcd for C21H18NO6 (M+H)+: 380.1129, found 380.1128.
Dimethyl 4ꢀ(4ꢀ(benzyloxy)benzoyl)quinolineꢀ2,3ꢀdicarboxylate (4e). CAS: 1374309ꢀ24ꢀ6. 48 mg, 35%, m. p.
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= 130ꢀ132oC, H NMR (400 MHz, CDCl3): 8.32 (d, J = 8.5 Hz, 1H), 7.88 (ddd, J = 8.4, 6.9, 1.3 Hz, 1H),
7.77ꢀ7.70 (m, 2H), 7.65ꢀ7.60 (m, 1H), 7.46ꢀ7.34 (m, 6H), 7.02 (d, J = 9.1 Hz, 2H), 5.14 (s, 2H), 4.08 (s, 3H),
3.70 (s, 3H). 13C NMR (100 MHz, CDCl3): 192.8, 166.2, 165.3, 163.7, 148.9, 148.2, 147.5, 135.7, 132.2,
131.8, 130.4, 129.7, 129.5, 128.6, 128.3, 127.4, 126.2, 124.6, 121.4, 115.0, 70.3, 65.8, 53.5, 53.3, 52.9, 52.8,
15.2. IR (cmꢀ1): 3070, 3039, 2957, 2362, 2319, 1740, 1669, 1599, 1575, 1509, 1458, 1438, 1313, 1250, 1200,
+
1168, 1129, 1074, 996, 839, 773, 741, 702, 643, 587. HRMS (ESI) m/z calcd for C27H22NO6 (M+H)+:
456.1442, found 456.1441.
Dimethyl 4ꢀ(4ꢀchlorobenzoyl)quinolineꢀ2,3ꢀdicarboxylate (4f). CAS: 1374309ꢀ26ꢀ8. 39 mg, 34%, m. p. =
92ꢀ94oC, 1H NMR (400 MHz, CDCl3): 8.32 (d, J = 8.5 Hz, 1H), 7.90 (ddd, J = 8.5, 4.6, 3.7 Hz, 1H), 7.74 (d,
J = 8.4 Hz, 2H), 7.67ꢀ7.60 (m, 2H), 7.46 (d, J = 8.8 Hz, 2H), 4.07 (s, 3H), 3.71 (s, 3H). 13C NMR (100 MHz,
CDCl3): 193.3, 166.2, 165.0, 149.2, 147.6, 141.0, 134.7, 132.4, 130.6, 130.5, 129.7, 129.3, 125.8, 124.3,
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