Med Chem Res (2013) 22:2755–2767
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General procedures for the synthesis of o-benzoyl-
N0-[(1E)-substituted-phenylmethylidene]benzohydrazides,
(4g–n)
4-Chloro-N0-[(1E)-2-hydroxy-naphthalen-1-ylmethylene)-
hydrazide, (4e) IR: 3290.00, 3200.00, 2978.09, 1606.70,
1650.00, 1554.44, 937.40, 611.00 cm-1; 1H NMR (DMSO):
d 8.0 (s, NH), 7.89 (d, 2H of Ph), 7.86 (d, 2H of Ph), 7.63 (m,
o-Benzoylbenzohydrazide 8 (0.0025 M) was dissolved in 1Hof Ph), 7.45 (d, 2H of Ph), 7.30 (m, 1H of Ph), 7.21 (m, 1H
methanol. In this substituted aromatic aldehyde (0.0025 M) of Ph), 6.8 (s, CH), 5.0 (s, OH); MS: m/z 324.05, 325.05
with three drops of glacial acetic acid was added. Mixture (M ? 1), 326.05 (M ? 2).
was refluxed for 4–5 h. The reaction was monitored by
TLC. The white-colored crude product was filtered out and 4-Chloro-N0-[(1E)-3-nitro-benzylidene)-hydrazide, (4f) IR:
recrystallized by a mixture of cold water and ethanol.
3201.63, 2953.00, 1651.00, 1665.00, 1529.55, 1558.00,
921.97, 663.00 cm-1;1H NMR (DMSO): d 8.4 (d, 2H of
Ph), 8.2 (d, 2H of Ph), 8.0 (s, of NH), 7.89 (d, 2H of Ph),
7.60 (m, 1H of Ph), 7.45 (d, 2H of Ph), 7.0 (s, CH); MS: m/
z 303.04, 304.04 (M ? 1), 305.04 (M ? 2).
Spectral data
Ethyl-4-chlorobenzoate IR: 3034.03, 1726.29, 1421.5,
1
837.11, 756.10 cm-1; H NMR (DMSO): 7.91 (d, 2H of
o-Benzoylbenzoic acid, (7) IR: 3360.00, 2930.00,
1
1680.00, 1530.00, 930.00; H NMR (DMSO): d 11 (s, 1H,
Ph), 7.38 (d, 2H of Ph), 4.29 (q, 2H of CH2), 1.30 (t, 3H of
CH3).
OH), 8.43 (d, 1H, Ar–H), 8.18 (d, 1H, Ar–H), 7.95 (d, 1H,
Ar–H), 7.80 (t, 1H, Ar–H), 7.63 (d, 2H, Ar–H), 7.61 (t, 1H,
Ar–H), 7.51 (t, 2H, Ar–H).
4-Chlorobenzohydrazide IR: 3277.06, 3159.40, 1456.21,
866.04, 738.74 cm-1; 1H NMR (DMSO): 9.9 (s, NH), 7.8-
7.9 (d, 2H of Ph), 7.4-7.6 (d, 2H of Ph), 4.6 (s, of NH2).
Ethyl-o-benzoylbenzoate, (8) IR: 3035.96, 1735.93,
1
1570.00, 1271.00, 947.05; H NMR (DMSO): d 8.33 (d,
1H, Ar–H), 8.02 (d, 1H, Ar–H), 7.82 (t, 1H, Ar–H), 7.70 (t,
1H, Ar–H), 7.64 (d, 2H, Ar–H), 7.62 (t, 1H, Ar–H), 7.52 (t,
2H, Ar–H), 4.31 (q, 2H, CH2), 1.30 (t, 3H, CH3).
4-Chloro-N0-[(1E)-2-hydroxyphenylmethylidene]benzohyd-
razides, (4a) IR: 3398.57, 3232.70, 3072.60, 1680.70,
1638.00, 1600.92, 860.25, 636.51 cm-1
;
1H NMR
(DMSO): d 7.9 (s, of NH), 7.8 (d, 2H of Ph), 7.7 (d, 2H of
Ph), 7.5 (d, 2H of Ph), 7.37 (d, 2H of Ph), 7.3 (s, CH), MS:
m/z 274.05, 275.05 (M ? 1), 276.05 (M ? 2).
o-Benzoylbenzohydrazide, (9) IR: 3487.00, 3053.32,
1541.00, 1843.00, 790.81; 1H NMR (DMSO): d 8.40 (d, 1H,
Ar–H), 7.86 (t, 1H, Ar–H), 7.79 (t, 1H, Ar–H), 7.77 (d, 1H, Ar–
H), 7.65 (d, 2H, Ar–H), 7.64 (t, 1H, Ar–H), 7.53 (t, 2H, Ar–H),
6.85 (s, 1H, of NH), 3.34 (s, 1H, of NH2), 1.78 (s, 1H, of NH2).
4-Chloro-N0-[(1E)-4-hydroxy-3-methoxyphenylmethylidene]
benzohydrazides, (4b) IR: 3387.80, 3250.05, 3014.74,
2912.00, 1409.00, 1620.21, 1670.00, 1577.77, 1276.00,
854.57, 611.00 cm-1; 1H NMR (DMSO): d 8.9 (s, of CH),
7.9 (s, of NH), 7.5 (d, 2H of Ph), 7.4 (s, OH), 7.3 (d, 2H of
Ph), 7.0 (d, 2H of Ph), 3.42 (s, of OCH3); MS: m/z 274.05,
275.05 (M ? 1), 276.05 (M ? 2).
o-Benzoyl-N’-[(1E)-phenylmethylidene]benzohydrazide,
(4g) IR: 3331.00, 3072.00, 1635.64, 1630.00, 1581.63,
817.82;1H NMR (DMSO): d 12.50 (s, 1H, –CONH), 8.40
(d, 1H, Ar–H), 7.93 (d, 2H, Ar–H), 7.86 (t, 1H, Ar–H), 7.79
(m, 1H, Ar–H), 7.78 (m, 1H, Ar–H), 7.63 (d, 2H, Ar–H),
7.61 (t, 1H, Ar–H), 7.58 (m, 3H, Ar–H), 7.52 (m, 2H, Ar–
H), 7.37 (s, 1H, CH), MS: m/z 328.12, 329.12 (M ? 1),
330.13 (M ? 2).
4-Chloro-N0-[(1E)-4-nitrophenylmethylidene]benzohydrazides,
(4c) IR: 3381.21, 3059.10, 1649.14, 1620.00, 1548.84,
1578.00, 821.68, 707.88 cm-1; 1H NMR (DMSO): d 8.1 (s,
of NH), 7.98 (d, 2H of Ph), 7.96 (d, 2H of Ph), 7.94 (d, 2H
of Ph), 7.7 (d, 2H of Ph), 7.1 (s, CH); MS: m/z 303.04,
304.04 (M ? 1), 305.04 (M ? 2).
o-Benzoyl-N’-[(1E)-4-chlorophenylmethylidene]benzohyd-
razide, (4h) IR: 3282.84, 3035.96, 1664.57, 1644.00,
1521.84, 885.33, 671.23; 1H NMR (DMSO): d 11.5 (s, 1H,
–CONH), 8.40 (d, 1H, Ar–H), 7.86 (t, 1H, Ar–H), 7.82 (d, 2H,
Ar–H), 7.80 (t, 1H, Ar–H), 7.64 (m, 2H, Ar–H), 7.61 (m, 1H,
Ar–H), 7.53 (t, 2H, Ar–H), 7.47 (d, 2H, Ar–H), 7.37(d, 1H,
Ar–H); MS: m/z 362.08, 363.09 (M ? 1), 364.08 (M ? 2).
4-Chloro-N0-[(1E)-4-methylphenylmethylidene]benzohyd-
razides, (4d) IR: 3402.43, 3107.00, 2974.00, 1629.85,
1627.00, 1563.00, 1344.00, 821.68, 726.00 cm-1; 1H NMR
(DMSO): d 7.8 (s, of NH), 7.7 (d, 2H of Ph), 7.6 (d, 2H of
Ph), 7.45 (d, 2H of Ph), 7.4 (d, 2H of Ph), 7.3 (s, CH), 2.4
(s, of CH3); MS: m/z 272.07, 273.07 (M ? 1), 274.07
(M ? 2).
o-Benzoyl-N’-[(1E)-4-nitrophenylmethylidene]benzohydrazide,
(4i) IR: 3429.00, 3072.00, 1655.00, 1633.71, 1556.50,
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