Regioselective synthesis of novel 2-chloroquinoline derivatives
at C-220), 4.13 (q, J = 7.2 Hz, 4 protons at C-9, 90), 5.06 (s, 1 proton at C-4), 5.71
(s, 1 proton at –NH), 6.54 (s, 1 proton at C-16), 7.03 (d, J = 8.0 Hz, 2 aryl protons
at C-13, 130), 7.13 (d, J = 8.0 Hz, 1 aryl proton at C-21), 7.41 (d, J = 8.0 Hz, 2 aryl
protons at C-12, 120), 7.49 (t, J = 7.0 Hz, 1 aryl proton at C-20), 7.86 (d,
J = 8.0 Hz, 1 aryl proton at C-19); 13C NMR (125 MHz, CDCl3) dC: 14.32 (C-10,
100), 19.53 (C-7, 70), 39.33 (C-4), 56.02 (C-220), 59.80 (C-9, 90), 103.90 (C-3, 5),
105.50 (C-16), 109.60 (C-21), 113.55 (C-19), 120.33 (C-13,130), 121.57 (C-18),
126.52 (C-20), 130.04 (C-12, 120), 140.37 (C-11), 144.22 (C-2, 6), 146.12 (C-23),
150.50 (C-17), 151.77 (C-14), 154.50 (C-22), 163.53 (C-15), 167.53 (C-8, 80); MS:
m/z Calcd. For C29H29ClN2O6: 536.1; found. 537.1 [M ? 1]; Anal Calcd for
C29H29ClN2O6: C 64.86, H 5.44, N 5.22; Found: C 65.01, H 5.54, N 5.17.
Diethyl 4-(4-(2-chloro-6-quinolines-4-yloxy)phenyl)-2,6-dimethyl-1,4-
dihydropyridine-3,5-dicarboxylate (3g)
Yield: 70 %. m.p.: 176 °C; IR (KBr, cm-1): 3,350 (–NH stretching), 2,979
(aromatic –CH stretching), 1,693 (–C=O); 1H NMR (200 MHz, CDCl3) dH: 1.25 (t,
J = 7.2 Hz, 6 protons at C-10, 100), 2.39 (s, 6 protons at C-7, 70), 4.14 (q,
J = 7.2 Hz, 4 protons at C-9, 90), 5.06 (s, 1 proton at C-4), 5.63 (s, 1 proton at
–NH), 6.52 (s, 1 proton at C-16), 7.02 (d, J = 8.0 Hz, 2 aryl protons at C-13, 130),
7.41 (d, J = 8.0 Hz, 2 aryl protons at C-12, 120), 7.52 (t, 1 aryl proton at C-21),
7.87–8.02 (m, 2 aryl protons at C-19, 22); 13C NMR (125 MHz, CDCl3) dC: 14.33
(C-10, 100), 19.67 (C-7, 70), 39.41 (C-4), 59.85 (C-9, 90), 104.06 (C-3, 5), 105.18
(C-16), 106.16 (C-19, J2C-F = 23.75 Hz), 120.30 (C-13, 130), 120.87 (C-21,
J2C-F = 23.75 Hz), 121.21 (C-18, JC3 -F = 12.5 Hz), 130.15 (C-12, 120), 130.66
(C-22, J3C-F = 10 Hz), 143.98 (C-2, 6), 145.62 (C-23), 146.26 (C-11), 150.61
(C-15), 151.53 (C-17), 159.47 (C-14), 162.26 (C-20, J1C-F = 206.25 Hz), 167.45
(C-8, 80); HRMS: m/z Calcd. For C28H26ClFN2O5: 524.1514; found. 524.1527 [M?].
Diethyl 4-(4-(2,7-dichloroquinolin-4-yloxy)phenyl)-2,6-dimethyl-1,4-dihydro
pyridine-3,5-dicarboxylate (3h)
Yield: 74 %. m.p.: 186–188 °C; IR (KBr, cm-1): 3,347 (–NH stretching), 2,978
(aromatic –CH stretching), 1,694 (–C=O); 1H NMR (200 MHz, CDCl3) dH: 1.25 (t,
J = 7.5 Hz, 6 protons at C-10, 100), 2.38 (s, 6 protons at C-7, 70), 4.12 (q,
J = 7.5 Hz, 4 protons at C-9, 90), 5.06 (s, 1 proton at C-4), 5.63 (s, 1 proton at
–NH), 6.48 (s, 1 proton at C-16), 7.01 (d, J = 8.0 Hz, 2 aryl protons at C-13, 130),
7.40 (d, J = 8.0 Hz, 2 aryl protons at C-12, 120), 7.67 (d, J = 8.0 Hz, 1 aryl proton
at C-20), 7.90 (d, J = 8.0 Hz, 1 aryl proton at C-19), 8.27 (s, 1 aryl proton at C-22);
13C NMR (125 MHz, CDCl3) dC: 14.33 (C-10, 100), 19.68 (C-7, 70), 39.42 (C-4),
59.85 (C-9, 90), 104.07 (C-3, 5), 105.36 (C-16), 120.28 (C-13, 130), 121.15 (C-18),
121.28 (C-19), 129.79 (C-20), 130.17 (C-12, 120), 132.00 (C-21), 132.37 (C-22),
143.96 (C-2, 6), 146.32 (C-11), 147.02 (C-23), 151.45 (C-17), 151.63 (C-14),
162.70 (C-15), 167.44 (C-8, 80); MS: m/z Calcd. For C28H26Cl2N2O5: 540.1; found.
541.1 [M ? 1]; Anal Calcd for C28H26Cl2N2O5: C 62.11, H 4.84, N 5.17; Found: C
62.60, H 4.75, N 5.08.
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