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m/z: 294 (M+H)+. Anal. Calcd for C17H15N3O2: C, 69.61; H, 5.15; N,
14.33. Found: C, 69.27; H, 5.44; N, 14.28.
5.2.10. 2-[(Quinolin-4-yl)methylene]-1-(7-methoxyquinolin-4-
yl)hydrazine (2k)
Yellow prisms, mp (EtOH) 252–254 °C. 1H NMR (DMSO-d6): d
3.94 (s, 3H), 7.38–7.44 (m, 2H), 7.55 (d, J = 6.8 Hz, 1H), 7.75–7.84
(m, 2H), 7.99 (d, J = 4.5 Hz, 1H), 8.10 (d, J = 8.1 Hz, 1H), 8.53–8.63
(m, 2H), 8.86 (d, J = 9.0 Hz, 1H), 8.99 (d, J = 4.5 Hz, 1H), 9.69 (s,
1H), 10.71 (br s, 1H). IR (Nujol) cmÀ1: 3366, 1620, 1239, 1050.
ESI-MS m/z: 329 (M+H)+. Anal. Calcd for C20H16N4O: C, 73.15; H,
4.91; N, 17.06. Found: C, 72.82; H, 4.74; N, 17.18.
5.2.4. 2-(3-Hydroxybenzylidene)-1-(7-methoxyquinolin-4-
yl)hydrazine (2d)
Yellow prisms, mp (EtOH) 265–267 °C. 1H NMR (DMSO-d6): d
3.88 (s, 3H), 6.78 (m, 2H), 7.12–7.26 (m, 5H), 8.18–8.27 (m, 2H),
8.48 (br s, 1H), 9.56 (s, 1H), 11.01 (br s, 1H). 13C NMR (DMSO-d6,
75 MHz): d 160.5, 158.4, 151.7, 151.2, 147.6, 143.3, 136.8, 130.5,
123.6, 118.7, 117.3, 117.2, 113.0, 112.1, 108.5, 100.3, 56.0. IR (Nu-
jol) cmÀ1: 3315, 1584, 1169. ESI-MS m/z: 294 (M+H)+. Anal. Calcd
for C17H15N3O2: C, 69.61; H, 5.15; N, 14.33. Found: C, 69.36; H,
5.38; N, 14.45.
5.2.11. 2-[(7-Methoxyquinolin-4-yl)methylene]-1-(7-methoxy-
quinolin-4-yl)hydrazine (2l)
Yellow prisms, mp (EtOH) 274–275 °C. 1H NMR (DMSO-d6): d
3.96 (s, 6H), 7.38–7.43 (m, 2H), 7.45 (d, J = 2.6 Hz, 1H), 7.49 (d,
J = 2.5 Hz, 1H), 7.52 (d, J = 6.3 Hz, 1H), 7.87 (d, J = 4.6 Hz, 1H),
8.52 (d, J = 9.2 Hz, 1H), 8.58 (br s, 1H), 8.83 (d, J = 8.1 Hz, 1H),
8.93 (d, J = 4.6 Hz, 1H), 9.63 (s, 1H), 11.25 (br s, 1H). IR (Nujol)
cmÀ1: 3137, 3065, 1626, 1458, 1450, 1234, 1166. ESI-MS m/z:
359 (M+H)+. Anal. Calcd for C21H18N4O2: C, 70.38; H, 5.06; N,
15.63. Found: C, 70.47; H, 5.41; N, 15.76.
5.2.5. 2-[(Benzo[d][1,3]dioxol-5-yl)methylene]-1-(7-methoxy-
quinolin-4-yl)hydrazine (2e)
Yellow prisms, mp (EtOH) 275–277 °C. 1H NMR (DMSO-d6): d
3.94 (s, 3H), 6.11 (s, 2H), 7.02 (d, J = 7.9 Hz, 1H), 7.26 (d,
J = 7.9 Hz, 1H), 7.36 (s, 1H), 7.37 (d, J = 7.4 Hz, 1H), 7.48 (s, 1H),
7.50 (d, J = 7.3 Hz, 1H), 8.49 (d, J = 7.4 Hz, 1H), 8.67 (s, 1H), 8.69
(d, J = 7.3 Hz, 1H), 11.01 (br s, 1H). IR (Nujol) cmÀ1: 3280, 1638,
1597, 1243, 1112. ESI-MS m/z: 322 (M+H)+. Anal. Calcd for
C18H15N3O3ÁHCl: C, 60.42; H, 4.51; N, 11.74. Found: C, 60.72; H,
4.65; N, 11.86.
5.2.12. 2-[(Benzo[d][1,3]dioxol-5-yl)methylene]-1-(7-ethoxy-
quinolin-4-yl)hydrazine (2n)
Yellow prisms, mp (EtOH) 257–259 °C. 1H NMR (DMSO-d6): d
1.48 (t, J = 8.2 Hz, 3H), 4.32 (q, J = 8.2 Hz, 2H), 6.11 (s, 2H), 6.98
(d, J = 7.2 Hz, 1H), 7.21 (d, J = 7.2 Hz, 1H), 7.34 (d, J = 7.4 Hz, 1H),
7.38 (br s, 1H), 7.50 (br s, 1H), 7.58 (d, J = 6.9 Hz, 1H), 8.47 (d,
J = 7.4 Hz, 1H), 8.59 (s, 1H), 8.62 (d, J = 6.9 Hz, 1H), 11.26 (br s,
1H). IR (Nujol) cmÀ1: 3182, 1461, 1376, 1149, 1110, 1067. ESI-
MS m/z: 336 (M+H)+. Anal. Calcd for C19H17N3O3ÁHCl: C, 61.38; H,
4.88; N, 11.30. Found: C, 61.49; H, 4.56; N, 11.48.
5.2.6. 2-(4-Dimethylaminobenzylidene)-1-(7-
methoxyquinolin-4-yl)hydrazine (2f)
Yellow prisms, mp (EtOH) 258–262 °C. 1H NMR (DMSO-d6): d
2.98 (s, 6H), 3.91 (s, 3H), 6.76 (d, J = 8.4 Hz, 2H), 7.28 (s, 1H), 7.29
(d, J = 6.6 Hz, 1H), 7.32 (d, J = 8.1 Hz, 1H), 7.62 (d, J = 8.4 Hz, 2H),
8.40 (d, J = 6.6 Hz, 1H), 8.55 (d, J = 8.1 Hz, 1H), 8.58 (s, 1H), 11.36
(br s, 1H). IR (Nujol) cmÀ1: 3120, 1456, 1376, 1179. ESI-MS m/z:
321 (M+H)+. Anal. Calcd for C19H20N4OÁ3/4 HCl: C, 65.63; H, 6.01;
N, 16.11. Found: C, 65.83; H, 6.25; N, 15.92.
5.2.13. 2-[(Pyridin-4-yl)methylene]-1-(7-ethoxyquinolin-4-
yl)hydrazine (2o)
Yellow prisms, mp (EtOH) 211–213 °C. 1H NMR (DMSO-d6): d
1.42 (t, J = 8.6 Hz, 3H), 4.18 (q, J = 8.6 Hz, 2H), 7.11 (d, J = 7.7 Hz,
1H), 7.26–7.34 (m, 2H), 7.69 (d, J = 5.6 Hz, 2H), 7.85 (d, J = 8.1 Hz,
1H), 8.36 (m, 2H), 8.59 (d, J = 5.2 Hz, 2H), 11.11 (br s, 1H). ESI-MS
m/z: 293 (M+H)+. IR (Nujol) cmÀ1: 3216, 1578, 1555, 1465. Anal.
Calcd for C17H16N4O: C, 69.85; H, 5.52; N, 19.17. Found: C, 69.78;
H, 5.76; N, 18.87.
5.2.7. 2-[(1H-Pyrrol-2-yl)methylene]-1-(7-methoxyquinolin-4-
yl)hydrazine (2g)
Yellow prisms, mp (EtOH) 136–138 °C. 1H NMR (DMSO-d6): d
3.86 (s, 3H), 6.10–6.14 (m, 1H), 6.40–6.43 (m, 1H), 6.91–6.93 (m,
1H), 7.07 (d, J = 8.7 Hz, 1H), 7.14 (s, 1H), 7.24 (d, J = 4.9 Hz, 1H),
8.14–8.18 (m, 3H), 10.73 (br s, 1H), 11.38 (s, 1H). IR (Nujol)
cmÀ1: 3341, 3197, 1582, 1231, 1122. ESI-MS m/z: 267 (M+H)+.
Anal. Calcd for C15H14N4O: C, 67.65; H, 5.30; N, 21.04. Found: C,
67.47; H, 5.64; N, 21.31.
5.2.14. 2-[(Quinolin-2-yl)methylene]-1-(2-methyl-7-methoxy-
quinolin-4-yl)hydrazine (2q)
Yellow prisms, mp (EtOH) 239–232 °C. 1H NMR (DMSO-d6): d
2.75 (s, 3H), 3.95 (s, 3H), 7.36–7.43 (m, 2H), 7.59 (s, 1H), 7.70 (d,
J = 8.1 Hz, 1H), 7.80 (t, J = 8.1 Hz, 1H), 8.00–8.10 (m, 2H), 8.35 (d,
J = 8.8 Hz, 1H), 8.45 (d, J = 8.1 Hz, 1H), 8.74 (d, J = 8.8 Hz, 1H), 8.93
(s, 1H), 12.90 (br s, 1H). IR (Nujol) cmÀ1: 3064, 1458, 1376, 1161,
1064. ESI-MS m/z: 343 (M+H)+. Anal. Calcd for C21H19N4OÁHCl: C,
65.84; H, 4.70; N, 15.36. Found: C, 65.58; H, 5.06; N, 15.17.
5.2.8. 2-[(Naphthalen-2-yl)methylene]-1-(7-methoxyquinolin-
4-yl)hydrazine (2h)
Yellow prisms, mp (EtOH) 208–210 °C. 1H NMR (DMSO-d6): d
3.87 (s, 3H), 7.11–7.35 (m, 3H), 7.52–7.57 (m, 2H), 7.91–7.98 (m,
3H), 8.02–8.12 (m, 2H), 8.26 (d, J = 8.2 Hz, 1H), 8.52 (m, 2H),
11.18 (br s, 1H). 13C NMR (DMSO-d6, 75 MHz): d 160.5, 151.8,
149.9, 147.7, 143.1, 134.1, 133.8, 133.4, 129.3, 129.1, 128.8,
128.4, 128.2, 127.4, 123.7, 123.3, 117.3, 112.1, 108.5, 100.5, 56.0;
5.2.15. 2-[(Quinolin-4-yl)methylene]-1-(2-methyl-7-methoxy-
quinolin-4-yl)hydrazine (2r)
IR (Nujol) cmÀ1
: 3483, 1623, 1312, 1121. ESI-MS m/z: 328
(M+H)+. Anal. Calcd for C21H17N3O: C, 77.04; H, 5.23; N, 12.84.
Found: C, 76.79; H, 5.01; N, 12.78.
Yellow prisms, mp (EtOH) 261–263 °C. 1H NMR (DMSO-d6): d
2.59 (s, 3H), 3.89 (s, 3H), 7.18–7.28 (m, 3H), 7.71–7.86 (m, 2H),
8.01 (d, J = 4.6 Hz, 1H), 8.08 (d, J = 8.1 Hz, 1H), 8.39 (d, J = 9.0 Hz,
1H), 8.58 (d, J = 8.0 Hz, 1H), 8.96 (d, J = 4.4 Hz, 1H), 9.24 (s, 1H),
12.75 (br s, 1H). IR (Nujol) cmÀ1: 3216, 1621, 1414, 1258, 1046.
ESI-MS m/z: 343 (M+H)+. Anal. Calcd for C21H18N4O: C, 73.67; H,
5.30; N, 16.36. Found: C, 73.32; H, 5.12; N, 16.55.
5.2.9. 2-[(6-Methoxynaphthalen-2-yl)methylene]-1-(7-meth-
oxyquinolin-4-yl)hydrazine (2i)
Yellow prisms, mp (EtOH) 238–240 °C. 1H NMR (DMSO-d6): d
3.88 (s, 6H), 7.18–7.21 (m, 3H), 7.35 (d, J = 2.3 Hz, 1H), 7.84–7.91
(m, 2H), 7.92–8.01 (m, 2H), 8.02 (s, 1H), 8.03 (d, J = 8.2 Hz, 1H),
8.25 (d, J = 9.0 Hz, 1H), 8.48 (s, 1H), 11.10 (br s, 1H). IR (Nujol)
cmÀ1: 3327, 1622, 1458, 1376, 1227, 1191. ESI-MS m/z: 358
(M+H)+. Anal. Calcd for C22H19N3O2: C, 73.93; H, 5.36; N, 11.76.
Found: C, 74.05; H, 5.69; N, 11.51.
5.2.16. 2-(4-Methoxybenzylidene)-1-(2-methyl-7-ethoxyquin-
olin-4-yl)hydrazine (2s)
Yellow prisms, mp (EtOH) 280–281 °C. 1H NMR (DMSO-d6): d
1.39 (t, 3H), 2.63 (s, 3H), 3.81 (s, 3H), 4.18 (q, 2H), 7.02 (d,