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8.19 (d, J=2.1 Hz, 1H), 8.92 (dd, J1=3.3 Hz,
J2=4.5 Hz, 1H).
J1=1.5 Hz, J2=4.8 Hz, 1H), 10.81 (s, 1H); IR (KBr):
3441, 3168, 1723, 1668, 1660, 1549, 1490, 1436, 1409,
1307, 1246, 1211, 1143, 1027, 980, 775, 700; HPLC
100%; EI-MS (m/z): 377 (10), 376 (M+, 45), 211 (15),
210 (100), 183 (10), 167 (15), 166 (25), 147 (35), 121 (10),
94 (35), 89 (30), 77 (15), 51 (10), 39 (10); HR-MS calcd
for C22H20N2O4: 376.1423. Found: 376.1419.
Ethyl
4-amido-(N-[3-phenoxylphenylacetyl)nicotinate
(12l). Mp92–93.5 ꢀC. 1H NMR d 1.41 (t, J=7.2 Hz,
3H), 3.77 (s, 2H), 4.37 (q, J=7.2 Hz, 2H), 7.20 (m, 9H),
8.58 (d, J=5.4 Hz, 1H), 8.66 (d, J=5.4 Hz, 1H), 9.14 (s,
1H), 11.24 (bs, 1H); IR (KBr): 3448, 3243, 3141, 2991,
1702, 1586, 1511, 1450, 1416, 1300, 1259, 1225, 1116,
802, 707, 543; HPLC 100%; EI-MS (m/z): 377 (20), 376
(M+, 80), 210 (65), 193 (40), 184 (25), 183 (35), 168
(10), 167 (65), 165 (70), 147 (100), 89 (30), 77 (20), 51
(10); HR-MS calcd for C22H20N2O4: 376.1423. Found:
376.1430.
8-Aza-4-hydroxy-3-(ꢀ30-phenoxy)phenylquinolin-2(lH)-one
1
(13n). Mp246–248 C (dec.). H NMR (DMSO-d6) d
7.09 (m, 6H), 7.23 (dd, J1=2.4 Hz, J2=7.8 Hz, 1H),
7.38 (m, 3H), 8.30 (d, J=7.8 Hz, 1H), 8.50 (d,
J=2.4 Hz, 1H), 10.52 (bm, 1H), 11.81 (s, 1H); IR (KBr)
3434, 3127, 1648, 1607, 1498, 1409, 1341, 1246, 1150,
946, 789, 761, 700, 571, 543, 475; HPLC 100%; EI-MS
(m/z): 332 (15), 331 (75), 330 (M+, 100), 121 (10), 93
(10), 77 (1 0), 51 (10), 39 (10); HR-MS calcd for
C20Hl4N2O3: 330.1004. Found: 330.1015.
6-Aza-4-hydroxy-3-(30-phenoxy)phenylquinolin-2(lH)-one
(13l). Mp165–167 ꢀC. H NMR (DMSO-d6) d 7.20 (m,
1
10 H), 8.47 (dd, J1=1.2 Hz, J2=3.6 Hz, 1H), 9.04 (s,
1H), 11.81 (s, 1H); IR (KBr): 3434, 3134, 1654, 1491,
1402, 1239, 1130, 700; HPLC 100%; LR-MS (m/z): 331
(30), 330 (M+, 100), 329 (100). 236 (20), 121 (40), 93
(40), 77 (50), 66 (20), 51 (40), 39 (25); HR-MS calcd for
C20H14N2O3: 330.1004. Found: 330.1002.
1
Ethyl 2-amido-(N-phenylacetyl)nicotinate (12o). Oil; H
NMR d 1.37 (t, J=6.9 Hz, 3H), 3.91 (s, 2H), 4.33 (q,
J=6.9 Hz, 2H), 7.04 (dd, J1=4.2 Hz, J2=7.5 Hz, 1H),
7.39 (m, 5H), 8.27 (dd, J1=0.9 Hz, J2=7.6 Hz, 1H),
8.60 (d, J=3.9 Hz, 1H), 10.76 (s, 1H).
Ethyl 3-aminoisonicotinate (9). Mp63–64 ꢀC (lit.15
65 ꢀC). 1H NMR d 1.40 (t, J=7.0 Hz, 3H), 4.37 (q,
J=7.0 Hz, 2H), 5.77 (d, J=1.2 Hz, 2H), 7.64 (d,
J=5.1 Hz, 1H), 7.91 (d, J=5.1 Hz, 1H), 8.25 (s, 1H).
8-Aza-4-hydroxy-3-phenylquinolin-2(lH)-one (13o). Mp
340–342 ꢀC. 1H NMR (DMSO-d6)
d
7.17 (dd,
J1=4.8 Hz, J2=7.8 Hz, 1H), 7.25 (m, 1H), 7.34 (t,
J=7.2 Hz, 2H), 7.42 (dd, J1=0.9 Hz, J2=7.2 Hz, 2H),
8.29 (dd, J1=1.2 Hz, J2=7.8 Hz, 1H), 8.45 (dd,
J1=1.2 Hz, J2=7.8 Hz, 1H), 11.64 (s, 1H); HPLC
99.2%; LR-MS (m/z): 239 (M+, 100), 238 (90), 181
(20), 121 (40), 118 (20), 93 (40), 91 (55), 89 (15), 77 (25),
69 (20), 63 (25), 57 (35), 55 (40), 51 (30), 43 (55), 41 (55);
HR-MS calcd for C14H10N2O2: 238.0742. Found:
238.0737.
Ethyl 3-amido-(N-[3-phenoxylphenylacetyl)isonicotinate
1
(12m). Oil; H NMR d 1.40 (t, J=7.2 Hz, 3H), 3.77 (s,
2H), 4.35 (q, J=7.2 Hz, 2H), 7.10 (m, 9H), 7.77 (d,
J=5.1 Hz, 1H), 8.41 (d, J=5.1 Hz, 1H), 10.01 (s, 1H),
10.65 (brs, 1H); IR (KBr): 3291, 3066, 2991, 1709, 1593,
1518, 1491, 1416, 1368, 1293, 1259, 1225, 1191, 1116,
1020, 973, 796, 768, 700; HPLC: 98.3%; EI–MS (m/z):
377 (15), 376 (M+, 70), 211 (15), 210 (100), 193 (25),
184 (20), 183 (45), 166 (25), 165 (15), 147 (40), 89 (20);
HR-MS calcd for C22H20N2O4: 376.1423. Found:
376.1430.
Ethyl 2-amido-[N-(3-phenoxy)phenylacetyl]-5-chloronico-
tinate (12p). Mp103–104 ꢀC. 1H NMR d 1.39 (t,
J=7.2 Hz, 3H), 3.88 (s, 2H), 4.35 (q, J=7.2 Hz, 2H),
7.10 (m, 9H), 8.24 (d, J=2.4 Hz, 1H), 8.52 (d,
J=2.4 Hz, 1H), 10.70 (d, J=2.4 Hz, 1H); IR (KBr)
3434, 3155, 2925, 1722, 1659, 1401, 1252, 1205, 1102,
775, 700; HPLC 99%; LR-MS (m/z): 41 0 (M+, 40), 211
(35), 210 (100), 200 (35), 183 (30), 181 (40), 128 (15), 89
(50), 77 (20), 51 (15); HR-MS calcd for C22Hl9ClN2O4:
410.1033. Found: 410.1026.
7-Aza-4-hydroxy-3-(30-phenoxy)phenylquinolin-2(1H)-
ꢀ
one (13m). Mp277–280 C (dec.). 1H NMR (DMSO-d6)
d 7.20 (m, 9H), 7.81 (d, J=5.4 Hz, 1H), 8.32 (d,
J=5.4 Hz, 1H), 8.62 (s, 1H), 10.65 (d, J=2.4 Hz, 1H),
11.74 (s, 1H); IR (KBr): 3427, 3148, 2936, 2861, 1661,
1614, 1498, 1402, 1307, 1252, 1225, 1198, 1136, 857,
700, 564; HPLC: 100%; LR-MS (m/z): 332 (20), 331
(90), 330 (M+, 100), 121 (15), 93 (15), 77 (10); HR-MS
calcd for C20Hl4N2O3: 330.1004. Found: 330.1018.
Anal. calcd for C20Hl4N2O3.H2O: C 69.0%, H 4.6%, N
8.0%. Found: C 69.3%, H 4.3%, N 7.7%.
8-Aza-6-chloro-4-hydroxy-3-(30-phenoxy)phenylquinolin-
2(l H)-one (13p). Mp237–240 ꢀC (dec.). 1H NMR
(DMSO-d6) d 7.10 (m, 9H), 8.33 (d, J=2.0 Hz, 1H),
8.54 (d, J=2.0 Hz, 1H), 10.70 (m, 1H), 12.04 (s, 1H); IR
(KBr): 3434, 3155, 1641, 1409, 1218, 1136, 1096; HPLC:
98.0%; LR-MS (m/z): 366 (25), 365 (45), 364 (M+, 80),
363 (100), 214 (30), 169 (15), 168 (10), 155 (15), 141 (15),
127 (15), 78 (30), 77 (30), 63 (40), 51 (30), 45 (10), 39
(10); HR-MS calcd for C20Hl3CN2O3: 364.0615. Found:
364.0606.
ꢀ
Ethyl 2-aminonicotinate (10). Mp90.5–92.5 C (lit.16 94–
95 ꢀC). 1H NMR d 1.38 (t, J=7.2 Hz, 3H), 4.34 (q,
J=7.2 Hz, 2H), 6.40 (bm, 2H), 6.62 (dd, J1=4.9 Hz,
J2=7.8 Hz, 1H), 8.14 (dd, Jl=1.0 Hz, J2=8.4 Hz, 1H),
8.21 (dd, J1=1.2 Hz, J2=3.8 Hz, 1H).
Ethyl
2-amido-[N-(3-phenoxy)phenylacetyl]nicotinate
Ethyl 2-amido-(N-phenylacetyl)-5-chloronicotinate (12q).
Mp113–114 ꢀC. 1H NMR d 1.38 (t, J=7.2 Hz, 3H),
3.90 (s, 2H), 4.34 (q, J=7.2 Hz, 2 H), 7.38 (m, 5H), 8.22
(d, J=2.4 Hz, 1H), 8.54 (d, J=2.4 Hz, 1H), 10.64 (s,
(12n). Mp90–91 ꢀC. 1H NMR d 1.39 (t, J=6.8 Hz,
3H), 3.83 (s, 2H), 4.35 (q, J=6.8 Hz, 2H), 7.10 (m, 9H),
8.29 (dd, J1=1.5 Hz, J2=7.8 Hz, 1H), 8.59 (dd,