4-Hydroxy(acyloxy)-3-methoxy(ethoxy)phenylmethylidene-(3-carboxyphenyl) amines

Article abstract of DOI:10.1134/S1070363206010166

Previously unknown Schiff bases were synthesized by reactions of 3-aminobenzoic acid with 4-hydroxy-3-methoxybenzaldehyde, 3-ethoxy-4- hydroxybenzaldehyde, and esters derived therefrom in methanol. Pleiades Publishing, Inc. 2006.

Full text of DOI:10.1134/S1070363206010166

ISSN 1070-3632, Russian Journal of General Chemistry, 2006, Vol. 76, No. 1, pp. 82 90.
Pleiades Publishing, Inc., 2006.
Original Russian Text
pp. 87 94.
E.A. Dikusar, N.G. Kozlov, V.I. Potkin, V.M. Zelenkovskii, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 1,
4-Hydroxy(acyloxy)-3-methoxy(ethoxy)phenylmethylidene-
(3-carboxyphenyl)amines
E. A. Dikusar, N. G. Kozlov, V. I. Potkin, and V. M. Zelenkovskii
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus,
ul. Surganova 13, Minsk, 220072 Belarus;
e-mail: loc@ifoch.bas-net.by
Received November 26, 2004
Abstract Previously unknown Schiff bases were synthesized by reactions of 3-aminobenzoic acid with
4-hydroxy-3-methoxybenzaldehyde, 3-ethoxy-4-hydroxybenzaldehyde, and esters derived therefrom in
methanol.
DOI: 10.1134/S1070363206010166
Schiff bases are widely used as biologically active
compounds, liquid crystalline substances, dyes,
luminophores, and polymer stabilizers [1 4]. Efficient
antidepressants, anticonvulsants, and antimicrobial,
hypnotic, psychotropic, nematocide, antiinflammatory,
antitumor, and other medical agents were designed on
the basis of Schiff bases [5, 6]. Due to the presence of
a polarized C=N bond, Schiff bases are convenient
starting compounds for the synthesis of heterocyclic
compounds [7] and -arylamino ketones which are
effective local anaesthetics [8, 9].
anhydrous methanol we obtained 3-[4-hydroxy(or
acyloxy)-3-methoxy(or ethoxy)phenylmethylidene-
amino]benzoic acids IIIa IIIz and IVa IVk. The
reactions were complete in 1.5 2 h under mild condi-
tions in the absence of a catalyst, so that the labile
ester group in the initial aldehydes was preserved.
The yields of Schiff bases IIIa IIIz and IVa IVk
were 90 94% (Table 1). Compounds IIIa IIIz and
IVa IVk may be promising from the viewpoints of
studying their biological, phototropic, and photo-
chromic properties, synthesis on their basis of va-
luable products and optical materials [6], and further
use in condensations with CH acids with a view to
obtain -arylamino ketones [8, 9].
The present article desribes the preparative synthesis
of previously unknown derivatives of accessible
natural hydroxy aldehydes (4-hydroxy-3-methoxy-
benzaldehyde and 3-ethoxy-4-hydroxybenzaldehyde)
and corresponding esters I. By condensation of
compounds I with 3-aminobenzoic acid (II) in boiling
The structure of Schiff bases IIIa IIIz and IVa
IVk was confirmed by their elemental compositions,
molecular weights (determined by titration; Table 1),
COOH
N
COOH
CHO
+
H2N
OR1
OR1
OR2
OR2
IIIa IIIy, IVa IVj
I
II
III, R1 = Me, R2 = H (a), C(O)Me (b), C(O)Et (c), C(O)Pr (d), C(O)Pr-i (e), C(O)(CH2)6Me (f), C(O)(CH2)8Me (g),
C(O)(CH2)11Me (h), C(O)(CH2)16Me (i), C(O)CH=CH2 (j), C(O)CMe=CH2 (k), C(O)(CH2)7CH=CH(CH2)7Me-cis (l),
C(O)CH2Ph (m), C(O)CH2CHMePh (n), C(O)(CH2)2OC6H4Me-4 (o), C(O)Ph (p), C(O)C6H4Me-4 (q), C(O)C6H4Cl-2 (r),
C(O)C6H4Cl-4 (s), C(O)C6H3Cl2-2,4 (t), C(O)CH2OC6H3Cl2-2,4 (u), C(O)CH2Br (v), C(O)CHBrCHBrPh (w),
C(O)C6H4Br-4 (x), C(O)C6H4NO2-3 (y); IV, R1 = Et, R2 = H (a), C(O)Me (b), C(O)Et (c), C(O)Pr (d), C(O)Pr-i (e),
C(O)CH2CHMe2 (f), C(O)Ph (g), C(O)C6H4Me-4 (h), C(O)C6H4Cl-2 (i), C(O)C6H4Cl-4 (j).
82

4-HYDROXY(ACYLOXY)-3-METHOXY(ETHOXY)PHENYLMETHYLIDENE-..
83
1
and H NMR, IR, and UV spectra (Table 2). Accord-
ing to the H NMR data, all the isolated compounds
COOH
1
HOOC
were almost pure E isomers (purity 98 1%). The
1
HC=N proton signal appeared in the H NMR spectra
N
N
of IIIa IIIz and IVa IVk as a singlet at 8.5 ppm.
The corresponding signal of the Z isomers is usually
located in a weaker field (by 0.5 ppm) due to the de-
shielding by the benzene ring containing the carboxy
group [10].
OR1
R1O
O
C
O
C
The steric structure of compounds IIIa IIIz and
IVa IVk was also confirmed by quantum-chemical
calculations of the heat of formation Hf of the E and
Z isomers of IIIa, IIIb, IIIp, IVa, IVb, and IVg
interms of MNDO PM3 semiempirical approximation
O
O
CH2 H2C
IIIz, IVj
IIIz, R1 = Me; IVk, R1 = Et.
Table 1. Yields, melting points, elemental analyses, and molecular weights of Schiff bases IIIa IIIz and IVa IVk
Found, %
H
Calculated, %
M
Comp. Yield,
mp,
C
Formula
no.
%
C
N
C
H
N
found
calculated
IIIa
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
IIIh
IIIi
90
91
92
90
93
90
92
90
91
90
92
90
93
91
94
94
93
92
93
91
92
90
90
92
92
94
90
91
92
90
92
92
136 137 66.74
165 166 65.48
143 144 66.36
117 118 67.08
128 129 67.14
5.07
5.07
5.43
5.74
5.80
6.98
7.52
8.11
9.05
4.80
5.19
8.70
5.16
5.70
5.48
4.63
5.08
4.09
4.20
3.61
3.82
3.65
3.52
3.67
4.05
4.71
5.48
5.28
5.74
6.11
6.12
6.46
4.96
4.21
4.10
3.88
3.92
3.42
3.04
2.70
2.34
4.09
3.79
2.31
3.27
3.11
2.98
3.58
3.29
3.17
3.22
2.90
2.71
3.29
2.33
2.90
6.34
4.18
4.65
3.90
3.76
3.75
3.70
3.62
C15H13NO4
C17H15NO5
C18H17NO5
C19H19NO5
C19H19NO5
C23H27NO5
C25H31NO5
C28H37NO5
C33H47NO5
C18H15NO5
C19H17NO5
C33H45NO5
C23H19NO5
C25H23NO5
C25H23NO6
C22H17NO5
C23H19NO5
C22H16ClNO5
C22H16ClNO5
C22H15Cl2NO5
C23H17Cl2NO6
C17H14BrNO5
C24H19Br2NO5
C22H16BrNO5
C22H16N2O7
C34H28N2O10
C16H15NO4
C18H17NO5
C19H19NO5
C20H21NO5
C20H21NO5
C21H23NO5
66.41
65.17
66.05
66.85
66.85
69.50
70.57
71.92
73.71
66.46
67.25
73.99
70.94
71.93
69.27
70.39
70.94
64.48
64.48
59.48
58.24
52.06
51.36
58.17
62.86
65.38
67.36
66.05
66.85
67.59
67.59
68.28
4.83
4.83
5.23
5.61
5.61
6.85
7.34
7.98
8.81
4.65
5.05
8.47
4.92
5.55
5.35
4.56
4.92
3.93
3.93
3.40
3.61
3.60
3.41
3.55
3.84
4.52
5.30
5.23
5.61
5.96
5.96
6.28
5.16
4.47
4.28
4.10
4.10
3.52
3.29
3.00
2.60
4.31
4.13
2.61
3.60
3.36
3.23
3.73
3.60
3.42
3.42
3.15
2.95
3.57
2.50
3.08
6.66
4.49
4.91
4.28
4.10
3.94
3.94
3.79
266.8
307.5
314.7
337.6
339.1
388.0
415.3
455.4
522.3
318.2
337.5
529.7
384.0
408.9
425.6
368.7
381.8
404.1
402.4
437.7
462.2
384.3
553.0
447.5
412.9
610.3
277.6
319.4
336.3
347.8
349.2
360.1
271.3
313.3
327.3
341.4
341.4
397.5
425.5
467.6
537.7
325.3
339.3
535.7
389.4
417.5
433.5
375.4
389.4
409.8
409.8
444.3
474.3
387.0
261.2
454.3
417.6
624.6
285.3
327.3
341.4
355.4
355.4
369.4
77 78
93 94
63 64
72 73
69.73
70.84
72.14
74.10
IIIj
IIIk
IIIl
194 105 66.72
174 175 67.68
57 58
156 157 71.25
68 69 72.16
74.32
IIIm
IIIn
IIIo
IIIp
IIIq
IIIra
IIIsb
IIItc
IIIud
IIIve
IIIwf
IIIxg
IIIy
IIIz
IVa
IVb
IVc
154 155 69.60
172 173 70.62
180 181 71.16
157 158 64.77
178 179 64.71
210 211 59.76
197 198 58.45
147 148 52.34
89 90
51.62
182 183 58.49
210 211 63.11
241 242 65.70
205 206 67.61
135 136 66.42
148 149 66.96
104 105 67.80
142 143 67.84
IVd
IVe
IVf
92 93
68.57
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84
DIKUSAR et al.
Table 1. (Contd.)
Found, %
H
Calculated, %
M
Comp. Yield,
mp,
C
Formula
no.
%
C
N
C
H
N
found
calculated
IVg
IVh
IVih
IVji
IVk
93
92
92
91
94
172 173 71.32
159 160 71.72
136 137 65.42
156 157 65.24
199 200 66.52
5.20
5.34
4.53
4.43
5.12
3.47
3.19
3.17
3.09
4.08
C23H19NO5
C24H21NO5
C23H18ClNO5
C23H18ClNO5
C36H32N2O10
70.94
71.45
65.18
65.18
66.25
4.92
5.25
4.28
4.28
4.94
3.60
3.47
3.30
3.30
4.29
382.6
394.7
414.8
419.0
644.5
389.4
403.4
423.9
423.9
652.7
a
b
c
Found Cl, %: 8.34. Calculated Cl, %: 8.65. Found Cl, %: 8.26. Calculated Cl, %: 8.65. Found Cl, %: 15.70. Calculated Cl, %:
d
e
f
15.96. Found Cl, %: 14.68. Calculated Cl, %: 14.95. Found Br, %: 20.04. Calculated Br, %: 20.37. Found Br, %: 28.08.
Calculated Br, %: 28.47. Found Br, %: 17.29. Calculated Br, %: 17.59. Found Cl, %: 8.12. Calculated Cl, %: 8.36. Found Cl,
%: 8.19. Calculated Cl, %: 8.36.
g
h
i
Table 2. IR, UV, and 1H NMR spectra of Schiff bases IIIa IIIz and IVa IVk
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IIIa 1800 3670 (OH); 3087, 3065, 3010 (CHAr and =CH); 205 (20000), 220 3.95 s (3H, CH3O), 6.50 br.s
2961, 2922, 2853, 2819 (CHAlk); 1658 (C=O); 1629 (C=N); (30000), 250 (12000), (1H, OH), 6.90 7.90 m (7H,
1584, 1518, 1591, 1481, 1457, 1418, 1364 (Ar); 1311, 307 (4000)
1267, 1250, 1220, 1168, 1129, 1118, 1034, 1023 (C O);
863, 837, 819, 787, 754, 738, 674, 640, 600 (CHAr)
C6H3 and C6H4), 8.54 s (1H,
HC=N), 9.90 s (1H, CO2H)
IIIb 2050 3640 (OH); 3100, 3085, 3070, 3040, 3005 (CHAr and 204 (17000), 221 2.27
s
(3H, CH3COO),
=CH); 2980, 2940, 2905, 2885, 2845, 2820 (CHAlk); 1740, (29000), 250 (10000), 3.88 s (3H, CH3O), 6.90
1697 (C=O); 1635 (C=N); 1597, 1578, 1511, 1460, 1450, 306 (3000)
1416, 1367 (Ar); 1309, 1277, 1235, 1218, 1200, 1153,
1123, 1080, 1035, 921 (C O); 860, 840, 815, 790, 762,
743, 692, 660, 630, 615, 600 (CHAr)
8.00 m (7H, C6H3 and C6H4),
8.60 s (1H, HC=N), 9.96 s
(1H, CO2H)
IIIc 2150 3640 (OH); 3090, 3080, 3060, 3035, 3005 (CHAr and 204 (18000), 221 1.27 t (3H, CH3CH2), 2.55 q
=CH); 2980, 2935, 2880, 2855, 2820 (CHAlk); 1744, 1698 (28000), 252 (11000), (2H, CH2), 3.88 (3H,
s
(C=O); 1631 (C=N); 1595, 1584, 1508, 1486, 1459, 1443, 306 (3000)
1416, 1372 (Ar); 1307, 1275, 1225, 1201, 1152, 1127,
1075, 1033, 987 (C O); 863, 838, 815, 789, 760, 744, 720,
688, 624 (CHAr)
CH3O), 6.90 8.02 m (7H,
C6H3 and C6H4), 8.60 s (1H,
HC=N), 9.97 s (1H, CO2H)
IIId 2140 3630 (OH); 3077, 3056, 2999 (CHAr and =CH); 205 (19000), 220 1.04 t (3H, CH3), 1.66 m
2965, 2936, 2922, 2876, 2852, 2835 (CHAlk); 1743, 1688 (28000), 252 (12000), (2H, CH2), 2.55 t (2H, CH2),
(C=O); 1632 (C=N); 1582, 1508, 1490, 1458, 1444, 1417, 306 (3000)
1380, 1372, 1349 (Ar); 1311, 1272, 1250, 1215, 1199,
1153, 1118, 1082, 1035, 973 (C O); 906, 866, 847, 818,
800, 785, 761, 743, 685, 621 (CHAr)
3.87 s (3H, CH3O), 6.90
8.04 m (7H, C6H3 and C6H4),
8.58 s (1H, HC=N), 9.97 s
(1H, CO2H)
IIIe 2100 3650 (OH); 3100, 3085, 3070, 3005 (CHAr and =CH); 204 (17000), 221 1.37
d
[6H, (CH3)2C],
2980, 2940, 2920, 2880, 2845, 2830 (CHAlk); 1746, 1688 (29000), 250 (10000), 2.90 kvintet (1H, CH),
(C=O); 1630 (C=N); 1596, 1575, 1504, 1460, 1452, 1416, 306 (3000)
1385, 1375, 1355 (Ar); 1297, 1274, 1220, 1198, 1181,
1152, 1133, 1117, 1102, 1032, 998, 969 (C O); 907, 866,
860, 818, 808, 782, 762, 743, 688, 669, 617 (CHAr)
3.87 s (3H, CH3O), 6.90
8.04 m (7H, C6H3 and C6H4),
8.58 s (1H, HC=N), 9.97 s
(1H, CO2H)
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4-HYDROXY(ACYLOXY)-3-METHOXY(ETHOXY)PHENYLMETHYLIDENE-..
85
Table 2. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IIIf 2000 3630 (OH); 3100, 3080, 3075, 3050, 3002 (CHAr and 205 (17000), 220 0.94 t (3H, CH3), 1.35 m
=CH); 2956, 2927, 2870, 2855 (CHAlk); 1762, 1697 (C=O); (29000), 250 (11000), [8H, (CH2)4], 1.80 m (2H,
1629 (C=N); 1601, 1586, 1578, 1512, 1455, 1416, 1380, 305 (3000)
1355 (Ar); 1316, 1289, 1276, 1268, 1215, 1200, 1160,
1132, 1110, 1030, 980 (C O); 920, 905, 866, 826, 808,
794, 762, 729, 688, 669, 617 (CHAr)
CH2), 2.60 m (2H, CH2),
3.88 s (3H, CH3O), 6.95
8.05 m (7H, C6H3 and C6H4),
8.60 s (1H, HC=N), 9.98 s
(1H, CO2H)
IIIg 2100 3620 (OH); 3100, 3080, 3070, 3012 (CHAr and 204 (18000), 220 0.92 t (3H, CH3), 1.20
=CH); 2951, 2924, 2870, 2855 (CHAlk); 1766, 1693, 1682 (29000), 250 (10000), 1.50 m [12H, (CH2)6], 1.87 t
(C=O); 1630 (C=N); 1600, 1580, 1511, 1455, 1416, 1380 306 (3000)
(Ar); 1321, 1286, 1266, 1220, 1200, 1175, 1132, 1110,
1080, 1060, 1034, 1000, 980 (C O); 905, 865, 840, 810,
795, 780, 762, 755, 720, 685, 660, 615 (CHAr)
(2H, CH2), 2.67 t (2H, CH2),
3.88 s (3H, CH3O), 6.90
8.05 m (7H, C6H3 and C6H4),
8.60 s (1H, HC=N), 9.97 s
(1H, CO2H)
IIIh 2150 3650 (OH); 3090, 3070, 3040, 3008 (CHAr and 204 (17000), 221 0.90 t (3H, CH3), 1.34 m
=CH); 2954, 2921, 2851 (CHAlk); 1762, 1698, 1683 (C=O); (29000), 250 (11000), [18H, (CH2)9], 1.78 m (2H,
1628 (C=N); 1600, 1582, 1509, 1486, 1465, 1454, 1418, 305 (3000)
1376 (Ar); 1315, 1273, 1198, 1150, 1119, 1108, 1076,
1060, 1031, 1000, 970 (C O); 896, 868, 825, 818, 800,
783, 759, 720, 680, 619 (CHAr)
CH2), 2.66 t (2H, CH2),
3.87 s (3H, CH3O), 6.95
8.10 m (7H, C6H3 and C6H4),
8.58 s (1H, HC=N), 9.98 s
(1H, CO2H)
IIIi
2150 3650 (OH); 3080, 3065, 3010 (CHAr and =CH); 204 (18000), 220 0.89 t (3H, CH3), 1.04
2955, 2917, 2849 (CHAlk); 1767, 1700, 1683 (C=O); 1631 (28000), 250 (10000), 1.90 [30H, (CH2)15],
m
(C=N); 1600, 1581, 1510, 1466, 1453, 1417, 1379, 1370 307 (3000)
(Ar); 1314, 1290, 1273, 1245, 1210, 1201, 1148, 1113,
1057, 1033 (C O); 917, 890, 875, 855, 840, 815, 795, 785,
756, 720, 685, 670, 620 (CHAr)
2.55 t (2H, CH2), 3.90 s (3H,
CH3O), 6.95 7.95 m (7H,
C6H3 and C6H4), 8.61 s (1H,
HC=N), 9.94 s (1H, CO2H)
IIIj 2130 3640 (OH); 3090, 3072, 3010 (CHAr and =CH); 205 (23000), 220 3.88 s (3H, CH3O), 5.82
2958, 2924, 2870, 2853 (CHAlk); 1762, 1691 (C=O); 1657 (32000), 252 (12000), 6.86 m (CH=CH2), 6.95
(C=C); 1630 (C=N); 1605, 1592, 1547, 1511, 1452, 1419, 306 (4000)
1366 (Ar); 1220, 1270, 1202, 1155, 1123, 1031, 980
(C O); 935, 900, 880, 860, 820, 755, 680, 665, 650 (CHAr
and =CH)
8.00 m (7H, C6H3 and C6H4),
8.60 s (1H, HC=N), 9.98 s
(1H, CO2H)
IIIk 2050 3640 (OH); 3100, 3080, 3060, 3040, 3005 (CHAr and 205 (24000), 221 2.08 t (3H, CH3), 3.89 s (3H,
=CH); 2980, 2970, 2960, 2940, 2880, 2840, 2820 (CHAlk); (32000), 250 (12000), CH3O), 5.82 t (1H, =CH),
1726, 1696 (C=O); 1632 1595, 1577, 1510, 1480, 1461, 305 (4000)
1450, 1415, 1375 (Ar); 1325, 1305, 1285, 1277, 1146,
1080, 1033, 970 (C O); 909, 870, 855, 820, 810, 790, 755,
740, 690, 675, 645, 635, 620, 605 (CHAr and =CH)
6.42 t (C=N); (1H, =CH),
7.00 8.05 m (7H, C6H3 and
C6H4), 8.60 s (1H, HC=N),
9.98 s (1H, CO2H)
IIIl
2350 3700 (OH); 3070, 3006 (CHAr and =CH); 2955, 206 (23000), 220 0.89 t (3H, CH3), 1.10
2925, 2854 (CHAlk); 1765, 1697 (C=O); 1658 (C=C); 1630 (32000), 250 (12000), 2.20 m [22H, (CH2)5 and
(C=N); 1600, 1584, 1508, 1465, 1418, 1376 (Ar); 1320, 306 (4000)
1273, 1199, 1152, 1120, 1035, 980 (C O); 920, 870, 820,
780, 759, 740, 723, 688, 665, 630 (CHAr and =CH)
(CH2)6], 2.62 t (2H, CH2),
3.88 s (3H, CH3O), 5.42 t
[2H, 2(=CH)], 6.95 8.10 m
(7H, C6H3 and C6H4), 8.60 s
(1H, HC=N), 9.98 s (1H,
CO2H)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 1 2006

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DIKUSAR et al.
Table 2. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IIIm 2100 3650 (OH); 3090, 3058, 3029, 3015, 2998 (CHAr and 207 (24000), 220 3.80 s (2H, CH2), 3.90 s (3H,
=CH); 2975, 2947, 2930, 2920, 2880, 2852, 2827 (CHAlk); (32000), 250 (11000), CH3O), 7.00 8.10 m (12H,
1764, 1687 (C=O); 1632 (C=N); 1595, 1577, 1505, 1460, 305 (3000)
1452, 1416, 1380, 1340 (Ar); 1303, 1274, 1232, 1219,
1198, 1151, 1134, 1117, 1077, 1031, 980, 946 (C O); 921,
906, 866, 840, 820, 790, 761, 745, 726, 715, 691, 680, 640,
620, 605 (CHAr)
C6H3, C6H4 and C6H5),
8.61 s (1H, HC=N), 10.02 s
(1H, CO2H)
IIIn 2300 3700 (OH); 2980, 2965, 3029, 3002 (CHAr and 206 (25000), 220 1.43 d (3H, CH3), 2.90 d
=CH); 2964, 2940, 2920, 2875, 2831 (CHAlk); 1758, 1695 (31000), 250 (11000), (2H, CH2), 3.42 q (1H, CH),
(C=O); 1631 (C=N); 1600, 1581, 1505, 1455, 1440, 1418, 305 (4000)
1369, 1355 (Ar); 1315, 1273, 1245, 1199, 1151, 1122,
1082, 1033, 980 (C O); 920, 870, 840, 825, 810, 780, 762,
740, 701, 689, 660, 620 (CHAr)
3.90 s (3H, CH3O), 6.98
8.08 m (12H, C6H3, C6H4
and C6H5), 8.60
s (1H,
HC=N), 10.00 s (1H, CO2H)
IIIo 2030 3650 (OH); 3090, 3075, 3045, 3020, 3008 (CHAr and 205 (25000), 222 2.30 s (3H, CH3), 3.12 t (2H,
=CH); 3080, 2935, 2920, 2882, 2856, 2830 (CHAlk); 1767, (35000), 250 (14000), CH2O), 3.89 s (3H, CH3O),
1700, 1679 (C=O); 1625 (C=N); 1609, 1582, 1463, 1447, 305 (5000)
1417, 1391, 1370 (Ar); 1315, 1294, 1273, 1249, 1222,
1197, 1159, 1147, 1116, 1075, 1045, 1026, 1012, 971
(C O); 912, 893, 871, 839, 827, 814, 783, 760, 739, 684,
674, 640, 621 (CHAr)
4.42 t (2H, CH2C=O), 6.98
8.08 m (11H, C6H3 and
2C6H4), 8.60 s (1H, HC=N),
9.98 s (1H, CO2H)
IIIp 2200 3630 (OH); 3080, 3040, 3007 (CHAr and =CH); 242 (22000), 250 3.90 s (3H, CH3O), 6.90
2960, 2935, 2920, 2880, 2840, 2830 (CHAlk); 1728, 1707 (12000), 207 (22000), 8.10 m (12H, C6H3, C6H4
(C=O); 1633 (C=N); 1596, 1580, 1509, 1454, 1417, 1380 220 (32000), 305 and C6H5), 8.64
s
(1H,
(Ar); 1295, 1270, 1260, 1205, 1185, 1157, 1125, 1081, (5000)
1066, 1040, 1025, 980 (C O); 920, 905, 870, 855, 830,
805, 780, 760, 740, 702, 680, 660, 640, 625 (CHAr)
HC=N), 10.04 s (1H, CO2H)
IIIq 2200 3650 (OH); 3085, 3070, 3008 (CHAr and =CH); 208 (19000), 221 2.46 s (3H, CH3), 3.89 s
2970, 2935, 2905, 2880, 2830 (CHAlk); 1727, 1706 (C=O); (36000), 252 (30000), (3H, CH3O), 7.00 8.10 m
1623 (C=N); 1608, 1602, 1579, 1515, 1464, 1442, 1420, 306 (6000)
1380, 1360 (Ar); 1321, 1298, 1263, 1202, 1175, 1162,
1121, 1104, 1074, 1029, 1015, 1002, 985 (C O); 931, 901,
874, 858, 840, 825, 800, 760, 748, 687, 661, 640, 620, 603
(CHAr)
(11H, C6H3 and 2C6H4),
8.62 s (1H, HC=N), 9.98 s
(1H, CO2H)
IIIr 2050 3650 (OH); 3100, 3075, 3005 (CHAr and =CH); 207 (37000), 221 3.90 s (3H, CH3O), 6.95
2965, 2925, 2880, 2820 (CHAlk); 1752, 1694 (C=O); 1627 (37000), 255 (20000), 8.26 m 2860, (11H, C6H3
(C=N); 1590, 1582, 1506, 1472, 1439, 1417, 1370 (Ar); 305 (5000)
1290, 1271, 1244, 1208, 1155, 1140, 1122, 1097, 1036,
980 (C O); 931, 900, 875, 860, 820, 780, 755, 739, 710,
681, 670, 650, 620 (CHAr); 550 (C Cl)
and 2C6H4), 8.64 s (1H,
HC=N), 10.04 s (1H, CO2H)
IIIs 2200 3650 (OH); 3098, 3080, 3055, 3006 (CHAr and 206 (36000), 221 3.92 s (3H, CH3O), 6.90
=CH); 2966, 2936, 2900, 2880, 2855, 2823 (CHAlk); 1738, (37000), 255 (19000), 8.24 m (11H, C6H3 and
1703 (C=O); 1624 (C=N); 1600, 1591, 1580, 1514, 1485, 305 (5000)
1464, 1442, 1417, 1400, 1361 (Ar); 1319, 1298, 1262,
1202, 1163, 1120, 1091, 1074, 1030, 1013, 985 (C O);
932, 900, 872, 859, 848, 824, 799, 760, 754, 708, 687, 680,
643, 613 (CHAr); 550 (C Cl)
2C6H4), 8.63 s (1H, HC=N),
10.04 s (1H, CO2H)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 1 2006

4-HYDROXY(ACYLOXY)-3-METHOXY(ETHOXY)PHENYLMETHYLIDENE-..
87
Table 2. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IIIt 2100 3640 (OH); 3097, 3073, 3027, 3008 (CHAr and 210 (43000), 221 3.90 s (3H, CH3O), 6.95
=CH); 2970, 2940, 2923, 2875, 2852, 2830 (CHAlk); 1751, (41000), 257 (24000), 8.50 m (10H, 2C6H3 and
1705 (C=O); 1627 (C=N); 1584, 1560, 1504, 1475, 1463, 306 (6000)
1440, 1417, 1374 (Ar); 1305, 1270, 1235, 1215, 1204,
1149, 1120, 1093, 1041, 1032, 980 (C O); 930, 895, 880,
850, 837, 815, 780, 756, 755, 680, 670, 640, 620 (CHAr);
545 (C Cl)
C6H4), 8.62 s (1H, HC=N),
10.04 s (1H, CO2H)
IIIu 2200 3630 (OH); 3100, 3072, 3040, 3000 (CHAr and 206 (40000), 220 3.90 s (3H, CH3O), 5.02 s
=CH); 2983, 2970, 2931, 2855 (CHAlk); 1786, 1717 (C=O); (34000), 251 (14000), (2H, CH2), 6.95 8.05
m
1623 (C=N); 1604, 1597, 1580, 1509, 1479, 1470, 1443, 305 (4000)
1422, 1393, 1375 (Ar); 1323, 1287, 1270, 1258, 1237,
1210, 1181, 1157, 1120, 1110, 1089, 1047, 1032, 1000,
986 (C O); 910, 866, 843, 821, 808, 780, 759, 741, 719,
690, 665, 646, 623 (CHAr); 541, 560 (C Cl)
(10H, 2C6H3 and C6H4),
8.64 s (1H, HC=N), 10.02 s
(1H, CO2H)
IIIv 2030 3630 (OH); 3100, 3061, 3012 (CHAr and =CH); 207 (20000), 221 3.90 s (3H, CH3O), 4.42 s
2966, 2931, 2895, 2876, 2851 (CHAlk); 1761, 1693 (C=O); (28000), 252 (12000), (2H, CH2), 7.04 8.00 m (7H,
1633 (C=N); 1597, 1578, 1509, 1480, 1462, 1447, 1415, 306 (4000)
1405, 1369 (Ar); 1308, 1274, 1214, 1194, 1172, 1153,
1123, 1085, 1033, 980, 970 (C O); 925, 907, 857, 813,
795, 760, 743, 688, 667, 640, 620 (CHAr); 540 (C Br)
C6H3 and C6H4), 8.59 s (1H,
HC=N), 9.98 s (1H, CO2H)
IIIw 2350 3700 (OH); 3065, 3040, 3006 (CHAr and =CH); 207 (25000), 221 3.91 s (3H, CH3O), 4.32 d
2960, 2939, 2920, 2880, 2833 (CHAlk); 1740, 1693 (C=O); (32000), 250 (12000), (1H, CH), 5.15 d (1H, CH),
1631 (C=N); 1601, 1504, 1463, 1448, 1418, 1377 (Ar); 306 (3000)
1315, 1275, 1238, 1194, 1181, 1151, 1120, 1077, 1050,
1031, 969 (C O); 920, 863, 840, 805, 780, 762, 740, 691,
605 (CHAr); 540 (C Br)
7.00 8.04 m (12H, C6H3,
C6H4 and C6H5), 8.60 s (1H,
HC=N), 10.02 s (1H, CO2H)
IIIx 2200 3600 (OH); 3096, 3080, 3070, 3040, 3004 (CHAr and 206 (35000), 220 3.90 s (3H, CH3O), 6.90
=CH); 2967, 2937, 2905, 2870, 2814 (CHAlk); 1736, 1703 (40000), 250 (20000), 8.10 m (11H, C6H3 and
(C=O); 1624 (C=N); 1600, 1580, 1514, 1481, 1464, 1442, 306 (5000)
1417, 1397, 1362 (Ar); 1320, 1299, 1262, 1203, 1163,
1120, 1074, 1029, 1009, 987 (C O); 900, 872, 859, 845,
823, 798, 762, 750, 700, 686, 678, 661, 642, 627, 612
(CHAr); 550 (C Br)
2C6H4), 8.63 s (1H, HC=N),
10.04 s (1H, CO2H)
IIIy 2050 3610 (OH); 3088, 3055, 3004 (CHAr and =CH); 205 (24000), 220 3.92 s (3H, CH3O), 6.95
2968, 2932, 2861, 2822 (CHAlk); 1743, 1692 (C=O); 1631 (54000), 260 (30000), 9.10 m (11H, C6H3 and
(C=N); 1620, 1595, 1582, 1507, 1446, 1415 (Ar); 1540, 305 (5000)
1348 (NO2); 1310, 1294, 1270, 1256, 1205, 1152, 1125,
1090, 1080, 1063, 1031, 1000 (C O); 920, 910, 890, 865,
820, 800, 785, 770, 715, 690, 680, 650, 630, 615 (CHAr)
2C6H4), 8.65 s (1H, HC=N),
10.06 s (1H, CO2H)
IIIz 2150 3650 (OH); 3100, 3081, 3005 (CHAr and =CH); 205 (34000), 220 3.06 s [4H, (CH2)2], 3.89 s
2973, 2941, 2927, 2881, 2849, 2830 (CHAlk); 1745, 1697 (55000), 251 (20000), (6H, 2CH3O), 7.00 8.00 m
(C=O); 1628 (C=N); 1603, 1579, 1505, 1480, 1473, 1456, 306 (5000)
1419, 1369 (Ar); 1310, 1276, 1259, 1212, 1197, 1153,
1139, 1117, 1091, 1031, 980 (C O); 915, 870, 840, 820,
790, 761, 748, 687, 660, 620, 611 (CHAr)
(14H, 2C6H3 and 2C6H4),
8.59 s (2H, 2HC=N), 9.99 s
(2H, CO2H)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 1 2006

88
DIKUSAR et al.
Table 2. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IVa 2000 3620 (OH); 3090, 3071, 3045, 3010 (CHAr and 204 (20000), 220 1.32 t (3H, CH3), 4.18 q
=CH); 2987, 2951, 2903, 2880, 2853, 2822 (CHAlk); 1686 (30000), 250 (12000), (2H, CH2), 6.50 br.s (1H,
(C=O); 1628 (C=N); 1604, 1590, 1583, 1509, 1448, 1400, 306 (4000)
1385 (Ar); 1308, 1290, 1269, 1249, 1215, 1195, 1181,
1155, 1118, 1075, 1032, 960, 935 (C O); 900, 880, 826,
783, 762, 750, 826, 783, 762, 750, 688, 670 (CHAr)
OH), 6.98 7.95
C6H3 and C6H4), 8.56 s (1H,
HC=N), 9.90 s (1H, CO2H)
m
(7H,
IVb 2000 3600 (OH); 3090, 3060, 3020, 3000 (CHAr and 204 (18000), 220 1.24 t (3H, CH3), 2.30 s (3H,
=CH); 2980, 2935, 2900, 2880, 2850, 2820 (CHAlk); 1748, (30000), 250 (10000), CH3COO), 4.12
q
m
(2H,
(7H,
1700 (C=O); 1633 (C=N); 1594, 1585, 1510, 1444, 1396, 306 (3000)
1368 (Ar); 1297, 1274, 1232, 1199, 1161, 1129, 1054,
1014, 1005, 983 (C O); 933, 915, 909, 859, 834, 792, 761,
748, 721, 679, 663, 625, 598 (CHAr)
CH2), 7.00 8.02
C6H3 and C6H4), 8.59 s (1H,
HC=N), 9.98 s (1H, CO2H)
IVc 2100 3620 (OH); 3080, 3059, 3010 (CHAr and =CH); 205 (19000), 220 1.28 t (3H, CH3), 1.42 t (3H,
2976, 2928, 2900, 2880, 2853, 2820 (CHAlk); 1748, 1690 (30000), 250 (11000), CH3), 2.70 q (2H, CH2),
(C=O); 1629 (C=N); 1584, 1506, 1441, 1432, 1393, 1380 305 (3000)
(Ar); 1295, 1272, 1230, 1196, 1160, 1122, 1085, 1060,
1044, 985, 974 (C O); 931, 909, 890, 875, 840, 815, 790,
760, 750, 682, 620, 602 (CHAr)
4.15 q (2H, CH2), 6.98
8.00 m (7H, C6H3 and C6H4),
8.60 s (1H, HC=N), 9.98 s
(1H, CO2H)
IVd 2130 3640 (OH); 3075, 3055, 3012 (CHAr and =CH); 204 (18000), 220 1.02 t (3H, CH3), 1.24 t (3H,
2976, 2935, 2900, 2879, 2850, 2830 (CHAlk); 1747, 1692 (29000), 250 (10000), CH3), 1.64 m (2H, CH2),
(C=O); 1629 (C=N); 1583, 1505, 1438, 1431, 1393, 1379, 305 (3000)
1367 (Ar); 1310, 1271, 1215, 1190, 1157, 1118, 1076,
1043, 1000, 972 (C O); 926, 908, 867, 842, 812, 798, 785,
1, 752, 683, 671, 618 (CHAr)
2.55 t (2H, CH2), 4.15 q
(2H, CH2), 7.02 8.04 m (7H,
C6H3 and C6H4), 8.59 s (1H,
HC=N), 9.98 s (1H, CO2H)
IVe 2030 3640 (OH); 3100, 3071, 3040, 3008 (CHAr and 205 (18000), 222
=CH); 2978, 2934, 2883, 2845, 2830 (CHAlk); 1747, 1690 (32000), 248 (11000), 1.24 t (3H, CH3), 2.90 quintet
(C=O); 1630 (C=N); 1591, 1575, 1504, 1471, 1448, 1428, 304 (4000)
1418, 1396, 1384, 1367, 1357 (Ar); 1308, 1296, 1272,
1212, 1196, 1180, 1158, 1132, 1116, 1102, 1039, 997, 967
(C O); 920, 910, 868, 818, 787, 762, 751, 687, 669, 656,
616 (CHAr)
2000 3700 (OH); 3075, 3010 (CHAr and =CH); 2990, 204 (18000), 221 1.10 d [6H, (CH3)2C], 1.24 t
2968, 2950, 2931, 2872, 2850, 2820 (CHAlk); 1746, 1687 (30000), 250 (10000), (3H, CH3), 1.42 2.90 m (3H,
(1H, CH), 1.34
d [6H,
(CH3)2C], 4.16 q (2H, CH2),
6.98 8.02 m (7H, C6H3 and
C6H4), 8.60 s (1H, HC=N),
9.98 s (1H, CO2H)
IVf
(C=O); 1627 (C=N); 1600, 1575, 1511, 1475, 1450, 1420, 305 (3000)
1396, 1370, 1350 (Ar); 1307, 1291, 1263, 1245, 1210,
1195, 1163, 1118, 1105, 1044, 981, 960 (C O); 920, 911,
880, 870, 850, 825, 760, 700, 682, 665, 640, 620 (CHAr)
CH and CH2), 4.10 q (2H,
CH2), 7.00 8.04 m (7H,
C6H3 and C6H4), 8.60 s (1H,
HC=N), 9.99 s (1H, CO2H)
IVg 2130 3630 (OH); 3095, 3080, 3061, 3031, 3005 (CHAr and 208 (22000), 220 1.26 t (3H, CH3), 4.20 q
=CH); 2983, 2955, 2916, 2900, 2866 (CHAlk); 1728, 1702 (31000), 241 (23000), (2H, CH2), 7.04 8.05
(C=O); 1633 (C=N); 1597, 1578, 1509, 1480, 1437, 1424, 250 (12000), 305 (12H, C6H3, C6H4 and
m
1395, 1377, 1365 (Ar); 1313, 1275, 1216, 1202, 1164, (5000)
1131, 1082, 1065, 1047, 1026, 995 (C O); 926, 909, 865,
858, 830, 805, 790, 764, 750, 720, 700, 691, 667, 630, 620
(CHAr)
C6H5), 8.64 s (1H, HC=N),
10.04 s (1H, CO2H)
IVh 2030 2680 (OH); 3100, 3075, 3040, 3007 (CHAr and 208 (20000), 221 1.28 t (3H, CH3), 2.48 s (3H,
=CH); 2990, 2970, 2950, 2935, 2900, 2880, 2840, 2820 (35000), 252 (30000), CH3), 4.12 q (2H, CH2),
(CHAlk); 1734, 1682 (C=O); 1627 (C=N); 1610, 1601, 306 (6000)
1574, 1510, 1475, 1449, 1422, 1397, 1360 (Ar); 1315,
1293, 1261, 1115, 1199, 1178, 1162, 1117, 1104, 1071,
1043, 1020, 972 (C O); 921, 910, 880, 870, 840, 830, 815,
805, 761, 745, 682, 660, 625, 605 (CHAr)
6.98 8.12 m (11H, C6H3 and
2C6H4), 8.62 s (1H, HC=N),
9.98 s (1H, CO2H)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 1 2006

4-HYDROXY(ACYLOXY)-3-METHOXY(ETHOXY)PHENYLMETHYLIDENE-..
89
Table 2. (Contd.)
Comp.
no.
UV spectrum,
max, nm ( )
1H NMR spectrum,
, ppm
1
IR spectrum, , cm
IVi
IVj
2000 2650 (OH); 3095, 3068, 3045, 3005 (CHAr and 207 (36000), 221 1.29 t (3H, CH3), 4.19 q (2H,
=CH); 2983, 2970, 2940, 2890, 2863, 2820 (CHAlk); 1757, (37000), 255 (21000), CH2), 7.00 8.26 m (11H,
1699 (C=O); 1630 (C=N); 1592, 1578, 1505, 1475, 1432, 305 (5000)
1413, 1387, 1360 (Ar); 1295, 1271, 1240, 1198, 1159,
1121, 1094, 1031, 980 (C O); 923, 908, 860, 825, 792,
760, 741, 688, 665, 645, 630, 620 (CHAr); 552 (C Cl)
C6H3 and 2C6H4), 8.65 s
(1H, HC=N), 10.02 s (1H,
CO2H)
2000 3670 (OH); 3071, 3004 (CHAr and =CH); 2987, 206 (36000), 221 1.29 t (3H, CH3), 4.20 q (2H,
2970, 2950, 2929, 2900, 2880, 2875, 2819 (CHAlk); 1734, (37000), 255 (20000), CH2), 7.02 8.28 m (11H,
1682 (C=O); 1627, 1610, 1600, 1580, 1574, 1511, 1480, 305 (5000)
1447, 1422, 1397, 1360 (Ar); 1318, 1293, 1261, 1230,
1200, 1178, 1162, 1117, 1105, 1071, 1043, 1020, 977
(C O); 925, 910, 875, 825, 810, 760, 745, 683, 670, 645,
630, 605 (CHAr); 560 (C Cl)
C6H3 and 2C6H4), 8.64 s
(1H, HC=N), 10.04 s (1H,
CO2H)
IVk 2130 3650 (OH); 3100, 3080, 3040, 3006 (CHAr and 205 (35000), 220 1.27 t (3H, CH3), 3.05 s [4H,
=CH); 2983, 2970, 2940, 2909, 2870, 2840, 2835 (CHAlk); (54000), 250 (20000), (CH2)2], 4.18 q (2H, CH2),
1744, 1693 (C=O); 1629 (C=N); 1602, 1590, 1587, 1504, 306 (5000)
1485, 1455, 1431, 1419, 1375, 1355 (Ar); 1310, 1271,
1260, 1215, 1190, 1150, 1137, 1115, 1084, 1038, 985
(C O); 918, 990, 980, 940, 915, 790, 761, 750, 690, 660,
625, 612 (CHAr)
6.98 8.00 m (14H, 2C6H3
and 2C6H4), 8.60 s (2H,
2HC=N), 9.98 s (2H, CO2H)
[11] using the GAMESS program [12]. The calcula-
tions were performed with full optimization of all bond
lengths and bond and dihedral angles. The following
3-[4-Hydroxy(or acyloxy)-3-methoxy(or
ethoxy)phenylmethylideneamino]benzoic acids
IIIa IIIz and IVa IVk (general procedure). 4-Hyd-
roxy-3-methoxybenzaldehyde, 3-ethoxy-4-hydroxy-
benzaldehyde, or the corresponding ester I, 0.01 mol,
was dissolved in 50 100 ml of anhydrous methanol,
0.01 mol of 3-aminobenzoic acid (II) (0.02 mol in the
synthesis of IIIz and IVk) was added, and the mixture
was heated for 1.5 2 h under reflux and left to
stand for 20 30 h at 20 23 C. The precipitate of
Schiff base IIIa IIIz or IVa IVk was filtered
through a glass filter, washed with a small amount of
methanol, and dried under reduced pressure. There
was no need of additionally purifying the products by
recrystallization. The solvent (methanol) can be reused
after distillation through a Vigreaux column.
1
data were obtained, Hf, kcal mol : E isomers: 101.1
(IIIa), 136.3 (IIIb), 100.4 (IIIp), 107.6 (IVa),
141.8 (IVb), 106.4 (IVg); Z isomers: 100.7 (IIIa),
135.6 (IIIb), 99.5 (IIIp), 106.1 (IVa), 141.3
(IVb), 105.5 (IVg). It is seen that the E configuration
1
is more favorable than Z by 0.4 1.5 kcal mol . The
results of calculations are in a good agreement with
the X-ray diffraction data for structurally related
compounds [13 15].
EXPERIMENTAL
The IR spectra were recorded in KBr on a Nicolet
Protege-460 Fourier spectrometer. The UV spectra
were measured on a Specord UV-Vis spectrophoto-
ACKNOWLEDGMENTS
4
1
meter from 10 M solutions in methanol. The H
NMR spectra were obtained on a Tesla BS-587A
instrument (100 MHz) from 5% solutions in DMSO-
d6 using octamethylcyclotetrasiloxane as internal
reference. The molecular weights were determined by
alkalimetric titration of the carboxy group with a
0.1 N solution of sodium hydroxide in the presence of
phenolphthalein as indicator. Initial esters I were
synthesized by the procedure described in [16].
This study was performed under financial support
by the Belorussian Republican Foundation for Basic
Research (project no. Kh03-079).
REFERENCES
1. Fedorov, B.S., Volyanskii, Yu.L., and Shevchuk, M.I.,
Khim.-Farm. Zh., 1978, vol. 12, no. 1, p. 77.
2. Bolotin, B.M., Etingen, N.B., Lastovskii, R.P., Ze-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 1 2006

90
DIKUSAR et al.
ryukina, L.S., and Safina, R.U., Zh. Org. Khim., 1977,
vol. 13, no. 2, p. 375.
nenii, Moscow: Khimiya, 1970, p. 92.
11. Stewart, J.J.P., J. Comput. Chem., 1989, vol. 10,
3. Krasovitskii, B.M., Smelyakova, V.B., and Nurmu-
khametov, R.N., Opt. Spektrosk., 1964, vol. 17, no. 3,
p. 558.
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