J. Chil. Chem. Soc., 60, Nº 1 (2015)
7.54 (m, 2H, ArH), 7.62-7.66 (m, 1H, ArH), 7.69 (d, 1H, J = 9.2 Hz, H-C(4)),
8.06-8.09 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ 48.84 (C(1¢)), 55.65
(MeO), 110.77, 115.36, 119.33, 121.50, 121.62, 128.10, 128.89, 133.96,
134.00, 134.84, 139.39, 154.79, 161.72 (C(2)), 192.54 (C(2¢)). Anal. Calcd
for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.65; H, 5.15; N, 4.68.
15b: 7 % yield. Mp 94-95 oC. 1H NMR (400 MHz, CDCl3): δ 3.88 (s, 3H,
MeO), 5.74 (s, 2H, H-C(1¢)), 7.04 (d, 1H, J = 2.4 Hz, H-C(5)), 7.08 (d, 1H, J
= 8.8 Hz, H-C(3)), 7.23 (dd, 1H, J = 8.8, 2.4 Hz, H-C(7)), 7.50-7.54 (m, 2H,
ArH), 7.60-7.62 (m, 1H, ArH), 7.63 (d, 1H, J = 8.8 Hz, H-C(8)), 7.95 (d, 1H,
J = 8.8 Hz, H-C(4)), 8.05-8.07 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ
55.75 (MeO), 67.74 (C(1¢)), 106.33, 113.10, 121.46, 126.23, 128.19, 128.70,
129.01, 133.76, 135.32, 138.57, 141.55, 156.52, 159.63 (C(2)), 194.95 (C(2¢)).
Anal. Calcd for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.78; H,
5.29; N, 4.60.
1H, J = 8.8 Hz, H-C(4)), 8.06-8.09 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3):
δ 55.64 (MeO), 67.78 (C(1¢)), 106.76, 110.24, 116.69, 120.47, 128.22, 128.66,
129.00, 133.77, 135.27, 139.16, 148.05, 161.20, 161.51 (C(2)), 194.75(C(2¢)).
Anal. Calcd for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.47; H,
5.24; N, 4.39.
7-Benzyloxy-1-(2-oxo-2-phenylethyl)quinolin-2(1H)-one (19a) and
7-Benzyloxy-2-(2-oxo-2-phenylethoxy)quinoline (19b)
Prepared from 7-benzyloxyquinolin-2(1H)-one and 2-bromoacetophenone
by the same procedure as described for 13a and 13b. 19a: 79 % yield. Mp
o
1
185-186 C. H NMR (400 MHz, CDCl3): δ 4.99 (s, 2H, CH O), 5.66 (s, 2H,
H-C(1¢)), 6.45 (d, 1H, J = 2.4 Hz, H-C(8)), 6.57 (d, 1H, J = 29.6 Hz, H-C(3)),
6.83 (dd, 1H, J = 8.8, 2.4 Hz, H-C(6)), 7.25-7.28 (m, 5H, ArH), 7.45 (d, 1H, J =
8.8 Hz, H-C(5)), 7.48-7.51 (m, 2H, ArH), 7.60-7.65 (m, 2H, ArH), 8.01 (d, 1H,
J = 9.6 Hz, H-C(4)), 8.02 -8.03 (m, 1H, ArH). 13C NMR (100 MHz, CDCl3): δ
49.19 (C(1¢)), 70.65 (CH O), 100.38, 110.55, 115.48, 118.30, 127.68, 128.41,
128.50, 128.94, 129.17, 2 130.67, 134.29, 135.07, 136.28, 139.98, 141.38,
161.21, 162.77 (C(2)), 192.65 (C(2¢)). Anal. Calcd for C24H19NO3: C, 78.03;
H, 5.18; N, 3.79. Found: C, 78.00; H, 5.21; N, 3.79.
6-Benzyloxy-1-(2-oxo-2-phenylethyl)quinolin-2(1H)-one (16a) and
6-Benzyloxy-2-(2-oxo-2-phenylethoxy)quinoline (16b)
Prepared from 6-benzyloxyquinolin-2(1H)-one and 2-bromoacetophenone
by the same procedure as described for 13a and 13b. 16a: 62 % yield. Mp
o
1
177-178 C. H NMR (400 MHz, CDCl3): δ 5.09 (s, 2H, CH O), 5.78 (s, 2H,
H-C(1¢)), 6.76 (d, 1H, J = 9.2 Hz, H-C(3)), 6.91 (d, 1H, J = 29.2 Hz, H-C(8)),
7.10 (d, 1H, J = 2.8 Hz, H-C(5)), 7.13 (dd, 1H, J = 8.8, 2.8 Hz, H-C(7)), 7.31-
7.44 (m, 5H, ArH), 7.51-7.55 (m, 2H, ArH), 7.63-7.68 (m, 2H, ArH), 8.07-8.09
(m, 1H, ArH), 8.08 (d, 1H, J = 9.2 Hz, H-C(4)). 13C NMR (100 MHz, CDCl ): δ
48.87 (C(1¢)), 70.55 (CH O), 112.19, 115.37, 119.98, 121.49, 121.77, 1273.42,
128.15, 128.66, 128.92, 2 133.99, 134.23, 134.84, 136.52, 139.39, 153.91,
161.77 (C(2)), 192.55 (C(2¢)). Anal. Calcd for C24H19NO3: C, 78.03; H, 5.18;
N, 3.79. Found: C, 77.68; H, 5.21; N, 3.66.
19b: 13 % yield. Mp 146-147 oC. 1H NMR (400 MHz, CDCl3): δ 5.12 (s,
2H, CH O), 5.77 (s, 2H, H-C(1¢)), 6.97 (d, 1H, J = 9.6 Hz, H-C(3)), 7.10 (dd,
1H, J =28.8, 2.4 Hz, H-C(6)), 7.17 (d, 1H, J = 2.4 Hz, H-C(8)), 7.32-7.42 (m,
3H, ArH), 7.44-7.47 (m, 2H, ArH), 7.51-7.55 (m, 2H, ArH), 7.61-7.66 (m,
2H, ArH), 7.97 (d, 1H, J = 8.8 Hz, H-C(5)), 8.06-8.09 (m, 1H, ArH), 8.07 (d,
1H, J = 9.6 Hz, H-C(4)). 13C NMR (100 MHz, CDCl3): δ 67.83 (C(1¢)), 70.29
(CH O), 107.91, 110.38, 117.04, 120.62, 127.88, 128.23, 128.33, 128.75,
128.286, 128.93, 129.01, 133.78, 135.30, 136.80, 139.19, 160.35, 161.51 (C(2)),
194.75 (C(2¢)). Anal. Calcd for C24H19NO3: C, 78.03; H, 5.18; N, 3.79. Found:
C, 78.40; H, 5.26; N, 3.71.
16b: 23 % yield. Mp 145-146 oC. 1H NMR (400 MHz, CDCl3): δ 5.14 (s,
2H, CH2O), 5.75 (s, 2H, H-C(1¢)), 7.09 (d, 1H, J = 8.8 Hz, H-C(3)), 7.13 (d,
1H, J = 2.8 Hz, H-C(5)), 7.32 (dd, 1H, J = 9.2, 2.8 Hz, H-C(7)), 7.34-7.37 (m,
1H, ArH), 7.38-7.43 (m, 2H, ArH), 7.46-7.49 (m, 2H, ArH), 7.51-7.54 (m, 2H,
ArH), 7.61-7.63 (m, 1H, ArH), 7.64 (d, 1H, J = 9.2 Hz, H-C(8)), 7.95 (d, 1H,
J = 8.8 Hz, H-C(4)), 8.05-8.08 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ
67.83 (C(1¢)), 70.54 (CH O), 107.82, 113.16, 121.91, 126.20, 127.78, 128.20,
128.32, 128.74, 128.88, 2 129.02, 133.77, 135.31, 136.95, 138.66, 141.61,
155.68, 159.71 (C(2)), 194.89 (C(2¢)). Anal. Calcd for C24H19NO3: C, 78.03;
H, 5.18; N, 3.79. Found: C, 78.00; H, 5.20; N, 3.78.
7-Chloro-1-(2-oxo-2-phenylethyl)quinolin-2(1H)-one
(20a)
and
7-Chloro-2-(2-oxo-2-phenylethoxy)quinoline (20b)
Prepared from 7-chloroquinolin-2(1H)-one and 2-bromoacetophenone by
the same procedure as described for 13a and 13b. 20a: 87 % yield. Mp 180-181
oC. 1H NMR (400 MHz, CDCl3): δ 5.76 (s, 2H, H-C(1¢)), 6.75 (d, 1H, J = 9.2
Hz, H-C(3)), 6.97 (d, 1H, J = 2.0 Hz, H-C(8)), 7.19 (dd, 1H, J = 8.4, 2.0 Hz,
H-C(6)), 7.52 (d, 1H, J = 8.4 Hz, H-C(5)), 7.55-7.59 (m, 2H, ArH), 7.66-7.71
(m, 1H, ArH), 7.72 (d, 1H, J = 9.2 Hz, H-C(4)), 8.09-8.12 (m, 2H, ArH). 13
C
NMR (100 MHz, CDCl3): δ 49.05 (C(1¢)), 114.37, 119.51, 121.49, 123.10,
128.46, 129.27, 130.34, 134.48, 134.87, 137.21, 139.57, 140.71, 162.15 (C(2)),
192.04 (C(2¢)). Anal. Calcd for C17H12NO2Cl·0.2H2O: C, 67.76; H, 4.14; N,
4.65. Found: C, 67.92; H, 4.02; N, 4.66.
6-Chloro-1-(2-oxo-2-phenylethyl)quinolin-2(1H)-one
(17a)
and
6-Chloro-2-(2-oxo-2-phenylethoxy)quinoline (17b)
Prepared from 6-chloroquinolin-2(1H)-one and 2-bromoacetophenone by
the same procedure as described for 13a and 13b. 17a: 64 % yield. Mp 213-
o
1
20b: 7 % yield. Mp 106-107 C. H NMR (400 MHz, CDCl ): δ 5.76 (s,
2H, H-C(1¢)), 7.10 (d, 1H, J = 8.8 Hz, H-C(3)), 7.32 (dd, 1H, J =38.4, 2.0 Hz,
H-C(6)), 7.51-7.55 (m, 2H, ArH), 7.62-7.66 (m, 1H, ArH), 7.64 (d, 1H, J = 8.4
Hz, H-C(5)), 7.70 (d, 1H, J = 2.4 Hz, H-C(8)), 8.01 (d, 1H, J = 8.8 Hz, H-C(4)),
8.03-8.06 (m, 2H, ArH). 13C NMR (100 MHz, CDCl ): δ 67.94 (C(1¢)), 113.26,
123.99, 125.46, 126.65, 128.16, 128.79, 129.10,3 133.94, 135.07, 135.65,
139.29, 146.75, 161.66 (C(2)), 194.31 (C(2¢)). Anal. Calcd for C17H12NO2Cl:
C, 68.58; H, 4.06; N, 4.70. Found: C, 68.22; H, 4.05; N, 4.64.
o
1
214 C. H NMR (200 MHz, CDCl ): δ 5.78 (s, 2H, H-C(1¢)), 6.78 (d, 1H, J
= 9.5 Hz, H-C(3)), 6.91 (d, 1H, J = 39.0 Hz, H-C(8)), 7.38 (dd, 1H, J = 9.0, 2.4
Hz, H-C(7)), 7.50-7.57 (m, 2H, ArH), 7.56 (d, 1H, J = 2.4 Hz, H-C(5)), 7.63-
7.67 (m, 1H, ArH), 7.87 (d, 1H, J = 9.5 Hz, H-C(4)), 8.05-8.10 (m, 2H, ArH).
13C NMR (50 MHz, CDCl ): δ 48.82 (C(1¢)), 115.57, 121,79, 122.54, 127.78,
128.09, 128.16, 129.00, 1330.65, 134.19, 134.69, 138.16, 138.72, 161.86 (C(2)),
192.07 (C(2¢)). Anal. Calcd for C17H12NO2Cl: C, 68.58; H, 4.06; N, 4.70.
Found: C, 68.47; H, 4.07; N, 4.77.
8-Methoxy-2-(2-oxo-2-phenylethoxy)quinoline (22b)
o
1
17b: 28 % yield. Mp 123-124 C. H NMR (400 MHz, CDCl ): δ 5.76
(s, 2H, H-C(1¢)), 7.13 (d, 1H, J = 8.8 Hz, H-C(3)), 7.49 (dd, 1H3, J = 8.8,
2.4 Hz, H-C(7)), 7.51-7.55 (m, 2H, ArH), 7.61-7.66 (m, 2H, ArH), 7.69 (d,
1H, J = 2.4 Hz, H-C(5)), 7.96 (d, 1H, J = 8.8 Hz, H-C(8)), 8.05 (d, 1H, J
= 8.8 Hz, H-C(4)), 8.04-8.06 (m, 1H, ArH). 13C NMR (100 MHz, CDCl3): δ
67.80 (C(1¢)), 114.06, 126.27, 126.54, 128.16, 129.01, 129.07, 129.94, 130.42,
133.89, 135.15, 138.56, 144.69, 160.14 (C(2)), 194.45 (C(2¢)). Anal. Calcd for
C17H12NO2Cl: C, 68.58; H, 4.06; N, 4.70. Found: C, 68.45; H, 4.08; N, 4.73.
7-Methoxy-1-(2-oxo-2-phenylethyl)quinolin-2(1H)-one (18a) and
7-Methoxy-2-(2-oxo-2-phenylethoxy)quinoline (18b)
Prepared from 8-methoxyquinolin-2(1H)-one and 2-bromoacetophenone
by the same procedure as described for 13a and 13b. 75 % yield. Mp 161-162
oC. 1H NMR (400 MHz, CDCl3): δ 3.88 (s, 3H, MeO), 5.80 (s, 2H, H-C(1¢)),
6.99-7.01 (m, 1H, ArH), 7.14 (d, 1H, J = 8.8 Hz, H-C(3)), 7.27-7.34 (m, 2H,
ArH), 7.49-7.54 (m, 2H, ArH), 7.59-7.63 (m, 1H, ArH), 8.03 (d, 1H, J = 8.8
Hz, H-C(4)), 8.07-8.10 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ 56.17
(MeO), 67.53 (C(1¢)), 109.54, 113.16, 119.66, 124.34, 126.55, 128.13, 128.65,
133.37, 135.46, 137.48, 139.42, 154.14, 160.16 (C(2)), 194.94 (C(2¢)). Anal.
Calcd for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.64; H, 5.19; N,
4.80.
Prepared from 7-methoxyquinolin-2(1H)-one and 2-bromoacetophenone
by the same procedure as described for 13a and 13b. 18a: 65 % yield. Mp
8-Benzyloxy-2-(2-oxo-2-phenylethoxy)quinoline (23b)
Prepared from 8-benzyloxyquinolin-2(1H)-one and 2-bromoacetophenone
by the same procedure as described for 13a and 13b. 91 % yield. Mp 132-133
oC. 1H NMR (400 MHz, CDCl3): δ 5.16 (s, 2H, CH O), 5.86 (s, 2H, H-C(1¢)),
7.07 (d, 1H, J = 8.8 Hz, H-C(3)), 7.15-7.28 (m,2 5H, ArH), 7.33-7.37 (m,
3H, ArH), 7.44-7.48 (m, 2H, ArH), 7.59-7.62 (m, 1H, ArH), 8.02-8.06 (m,
2H, ArH), 8.05 (d, 1H, J = 8.8 Hz, H-C(4)). 13C NMR (100 MHz, CDCl3): δ
67.81 (C(1¢)), 71.38 (CH O), 112.83, 113.26, 120.62, 124.48, 126.94, 127.16,
127.72, 128.15, 128.53, 2 128.71, 129.02, 133.71, 135.27, 137.61, 139.65,
153.42, 160.31 (C(2)), 194.62 (C(2¢)). Anal. Calcd for C24H19NO3: C, 78.03;
H, 5.18; N, 3.79. Found: C, 78.01; H, 5.17; N, 3.61.
o
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171-172 C. H NMR (400 MHz, CDCl3): δ 3.78 (s, 3H, MeO), 5.76 (s, 2H,
H-C(1¢)), 6.44 (d, 1H, J = 2.4 Hz, H-C(8)), 6.60 (d, 1H, J = 9.2 Hz, H-C(3)),
6.80 (dd, 1H, J = 8.8, 2.4 Hz, H-C(6)), 7.49 (d, 1H, J = 8.8 Hz, H-C(5)), 7.51-
7.55 (m, 2H, ArH), 7.63-7.65 (m, 1H, ArH), 7.68 (d, 1H, J = 9.6 Hz, H-C(4)),
8.07-8.10 (m, 2H, ArH). 13C NMR (100 MHz, CDCl3): δ 49.14 (C(1¢)),
55.74 (MeO), 99.42, 109.60, 115.34, 118.24, 128.38, 129.18, 130.69, 134.25,
135.14, 139.98, 141.45, 162.08, 162.77 (C(2)), 192.95 (C(2¢)). Anal. Calcd
for C18H15NO3: C, 73.71; H, 5.15; N, 4.78. Found: C, 73.70; H, 5.17; N, 4.78.
18b: 12 % yield. Mp 137-138 oC. 1H NMR (400 MHz, CDCl3): δ 3.87 (s,
3H, MeO), 5.77 (s, 2H, H-C(1¢)), 6.96 (d, 1H, J = 8.8 Hz, H-C(3)), 7.01 (dd,
1H, J = 8.8, 2.4 Hz, H-C(6)), 7.07 (d, 1H, J = 2.4 Hz, H-C(8)), 7.50-7.55 (m,
2H, ArH), 7.59 (d, 1H, J = 9.2 Hz, H-C(5)), 7.61-7.65 (m, 1H, ArH), 7.96 (d,
8-Chloro-2-(2-oxo-2-phenylethoxy)quinoline (24b)
Prepared from 8-chloroquinolin-2(1H)-one and 2-bromoacetophenone by
the same procedure as described for 13a and 13b. 94 % yield. Mp 183-184 oC.
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