ACCEPTED MANUSCRIPT
8 Hz), 4.25 (q, 2H, J = 6.4 Hz), 1.80-1.71 (m, 2H), 1.47-1.33 (m, 6H), 1.09 (t, 3H, J = 6.8 Hz), 0.92 (t,
3H, J = 7.3 Hz). 13C NMR (CDCl3, 100 MHz) δ: 172.09, 134.01, 125.80, 122.45, 114.37, 42.55, 31.55,
27.67, 26.70, 22.62, 14.01, 10.52. EI-MS: 450 [M+H]+, 473 [M+Na]+. M.p.: 103-108 °C LC/MS: RT
5.32 min; 473 [M+Na]+. Purity: 98%. Anal calcd for C26H30N2O5 C, H, N: C 69.31, H 6.71, N 6.22, O
17.76; found C 69.28, H 6.67, N 6.20.
Propyl 3-methyl-5-(1-hexyl-4-hydroxy-2-oxo-1,2dihydroquinolin-3-carboxamido)-benzoate (22).
Yield: 48%. 1H NMR (CDCl3, 200 MHz): δ 17.01 (bs, 1H), 12.45 (bs, 1H), 8.30 (d, 1H, J = 4.6 Hz), 8.22
(d, 1H, J = 3.8 Hz), 7.89 (s, 1H), 7.67 (t, 2H, J = 4 Hz), 7.34-7.24 (m, 2H), 4.34 (q, 2H, J = 6.8 Hz), 4.25
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(t, 2H, J = 6.5 Hz), 2.47 (s, 3H), 1.80-1.68 (m, 2H), 1.59-1.32 (m, 8H), 1.10-0.80 (m, 6H). C NMR
(CDCl3, 50 MHz): δ 172.05, 169.71, 140.12, 134.02, 131.67, 128.23, 125.77, 122.39, 121.33, 114.37,
66.38, 42.30, 31.50, 27.56, 26.59, 22.60, 22.13, 18.47, 14.01, 10.53.EI-MS: 465 [M+H]+, 487
[M+Na]+. M.p.: 120-122 °C. LC/MS: RT 5.98 min; 465 [M+H]+, 487 [M+Na]+. Purity: 99%. Anal calcd
for C27H32N2O5 C, H, N: C 69.81, H 6.94, N 6.03, O 17.22; found C 69.84, H 6.95, N 6.02.
tert-Butyl 3-(1-hexyl-4-hydroxy-2-oxo-1,2dihydroquinolin-3-carboxamido)-benzoate (23). Yield:
1
32%. H NMR (CDCl3, 4OO MHz): δ 16.45 (bs, 1H), 12.39 (bs, 1H), 8.80 (d, 1H, J= 6.8 Hz), 7.91 (d,
1H, J = 7.6 Hz), 7.75 (d, 1H J = 7.6 Hz), 7.66 (t, 1H, J = 7.6 Hz), 7.39 (t, 1H, J = 8 Hz), 7.30 (d, 1H, J =
1.2 Hz), 7.26 (dd, 2H, J1 = 8 Hz, J2 = 7.6 Hz,), 4.24 (t, 2H, J = 6.4 Hz), 1.58-1.33 (m, 6H), 1.23 (s, 9H),
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0.89 (t, 3H, J = 6.8 Hz). C NMR (CDCl3, 100 MHz): δ 172.04, 169.63, 165.33, 165.33, 162.51,
138.20, 137.31, 133.98, 132.94, 128.82, 125.76, 125.67, 125.17, 122.41,122.14, 116.30, 114.35,
97.03, 81.24, 42.52, 31.54, 30.89, 29.70, 28.22, 27.66, 26.69, 22.62, 14.02. ES-MS: 465 [M+H]+, 487
[M+Na]+. M.p.: 120-125 °C. LC/MS: RT 5.72 min; 465 [M+H]+, 487 [M+Na]+. Purity: 97%. Anal calcd
for C27H32N2O5 C, H, N: C 69.81, H 6.94, N 6.03, O 17.22; found C 69.83, H 6.97, N 6.00.
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Ethyl 3-(1-hexyl-4-hydroxy-2-oxo-1,2dihydroquinolin-3-carboxamido)-benzoate (24) Yield: 58%. H
NMR (CDCl3, 400 MHz): δ 16.39 (bs, 1H), 12.57 (bs, 1H), 8.28 (d, 1H, J = 8 Hz), 7.98 (d, 1H, J =8 Hz),
7.82 (d, 1H, J = 8 Hz), 7.68 (t, 1H, J = 8 Hz,), 7.42 (t, 1H, J = 8 Hz), 7.35-7.27 (m, 2H), 4.38 (q, 2H, J =
8 Hz), 4.25 (t, 2H, J = 8 Hz,), 1.77-1.69 (m, 4H), 1.56-1.35 (m, 7H), 0.92 (t, 3H, J = 8 Hz,).13C NMR
(CDCl3, 100 MHz): δ 169.65, 139.22, 134.02, 131.39, 129.02, 125.80, 125.49, 122.46, 122,16,
114.38, 97.05, 61.14, 42.56, 31.56, 27.67, 26.70, 22.62, 14.38, 14.02. EI-MS: 437 [M+H]+, 459
[M+Na]+. M.p.: 70-73 °C. LC/MS: RT 5.07 min; 437 [M+H]+, 459 [M+Na]+. Purity: 97%. Anal calcd for
C25H28N2O5 C, H, N: C 68.79, H 6.47, N 6.42, O 18.33; found C 68.82, H 6.45, N 6.41.
Propyl 2-chloro-5-(1-hexyl-4-hydroxy-2-oxo-1,2dihydroquinolin-3-carboxamido)-benzoate (26).
Yield: 46%. 1H NMR (CDCl3, 400 MHz): δ 16.21 (bs, 1H), 13.12 (bs, 1H), 8.23 (d, 1H, J = 8 Hz), 7.85 (t,
1H, J = 12 Hz), 7.67 (t, 1H, J = 7.64 Hz), 7.58 (d, 2H, J = 8 Hz), 7.34-7.24 (m, 2H), 4.23 (q, 4H, J = 7.2
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Hz), 1.82-1.69 (m, 2H), 1.58-1.30 (m, 6H), 1.03 (t, 3H, J = 6.8 Hz,), 0.89 (t, 3H, J = 7.6 Hz). C NMR
(CDCl3, 100 MHz): δ 172.10, 162.47, 141.10, 139.22 134.93, 134.27, 132.50, 125.83, 125.34,
122.72, 118.41, 114.42, 97.00, 67.00, 42.63, 31.53, 27.63, 26.68, 22.61, 22.05, 14.02, 10.62. EI-MS:
485 [M+H]+, 507 [M+Na]+. M.p.: 110-113 °C. LC/MS: RT 4.38 min; 485 [M+H]+, 507 [M+Na]+. Purity:
99%. Anal calcd for C26H29ClN2O5 C, H, N: C 64.39, H 6.03, Cl 7.31, N 5.78, O 16.50; found C 64.38, H
6.05, N 5.75.
Propyl 3-trifluoromethyl-4-(1-hexyl-4-hydroxy-2-oxo-1,2dihydroquinolin-3-carboxamido)-benzoate
(27). Yield: 56%. 1H NMR (CDCl3, 200 MHz): δ 16.21 (bs, 1H), 12.31 (bs, 1H), 8.47 (s, Hz, 1H), 8.46 (s,
1H), 8.39 (d, 1H, J= 4.4 Hz), 8.33 (s, 1H), 8.20 (d, 1H, J = 4.4 Hz), 7.68 (t, 1H, J = 4.6 Hz), 7.34-724 (m,
1H), 4.39-4.25 (m, 4H), 1.82-1.87 (m, 2H), 1.46-1.18 (m, 2H), 1.05-1.0 (m, 6H), 0.90-0.87 (m, 3H),