(C=O); 1622 (C=N); 1591, 1507, 1464, 1421, 1397, 1354 (Ar); 1320, 1287, 1242, 1201, 1154, 1121, 1075, 1056, 1033, 991
(C–O); 888, 860, 847, 830, 800, 785, 762, 750, 693, 650, 640, 630, 615 (CH ).
Ar
PMR spectrum (δ, ppm): 1.28 (CH , t), 2.55 (CH , q), 3.88 (CH O, s), 6.30-7.75 (C H and C H , m), 8.10 and 8.20
3
2
3
6
3
6 4
(HC=N, s and s), 9.94 (CO H, s).
2
4-p-Butyryloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3d). Yield90%, mp112-113°C, C H NO .
19 19
5
-1
IR spectrum (ν, cm ): 2030-3650 (OH); 3085, 3070, 3040, 3010 (=CH and CH ); 2990, 2956, 2932, 2880, 2850, 2835
Ar
(CH ); 1763, 1707 (C=O); 1628 (C=N); 1600, 1590, 1508, 1455, 1422, 1410, 1390, 1381 (Ar); 1281, 1242, 1203, 1158, 1137,
Alk
1124, 1099, 1054, 1032, 1003, 995 (C–O); 846, 840, 803, 775, 750, 698, 660, 630, 620 (CH ).
Ar
PMR spectrum (δ, ppm): 1.04 (CH , t), 1.65 (CH , m), 2.55 (CH , t), 3.88 (CH O, s), 6.30-7.80 (C H and C H , m),
3
2
2
3
6
3
6 4
8.10 and 8.20 (HC=N, s and s), 9.96 (CO H, s).
2
4-i-Butyryloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3e). Yield91%, mp126-127°C, C H NO .
19 19
5
-1
IR spectrum (ν, cm ): 2100-3650 (OH); 3080, 3070, 3035, 3020 (=CH and CH ); 2970, 2939, 2875, 2854, 2840 (CH );
Ar
Alk
1755, 1705 (C=O); 1624 (C=N); 1597, 1506, 1466, 1450, 1421, 1398, 1380 (Ar); 1282, 1242, 1220, 1202, 1183, 1157, 1127,
1096, 1030, 1004, 975 (C–O); 861, 848, 819, 790, 775, 762, 743, 693, 650, 616 (CH ).
Ar
PMR spectrum (δ, ppm): 1.34 [(CH ) C, d], 2.81 (CH, m), 3.89 (CH , s), 6.40-7.90 (C H and C H , m), 8.12 and
3 2
3
6
3
6 4
8.25 (HC=N, s and s), 9.96 (CO H, s).
2
4-n-Capryloyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3f). Yield94%, mp65-66°C, C H NO .
23 27
5
-1
IR spectrum (ν, cm ): 2100-3650 (OH); 3085, 3074, 3045, 3015 (=CH and CH ); 2955, 2930, 2856 (CH ); 1757, 1698
Ar
Alk
(C=O); 1619 (C=N); 1594, 1508, 1488, 1465, 1421, 1378 (Ar); 1323, 1278, 1253, 1243, 1200, 1156, 1145, 1122, 1101, 1056,
1032, 995 (C–O); 870, 845, 830, 803, 780, 756, 740, 695, 655, 640, 620 (CH ).
Ar
PMR spectrum (δ, ppm): 0.94 (CH , t), 1.35 [(CH ) , m], 1.82 (CH , m), 2.60 (CH , m), 3.89 (CH O, s), 6.40-7.88
3
2 4
2
2
3
(C H and C H , m), 8.12 and 8.24 (HC=N, s and s), 9.95 (CO H, s).
6
3
6
4
2
4-n-Caprinoyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3g).
Yield 93%, mp 105-106°C,
-1
C H NO . IR spectrum (ν, cm ): 2030-3620 (OH); 3080, 3060, 3040, 3010 (=CH and CH ); 2954, 2924, 2853 (CH );
25 31
5
Ar
Alk
1753, 1699 (C=O); 1622 (C=N); 1596, 1507, 1466, 1450, 1420, 1397, 1377 (Ar); 1320, 1279, 1242, 1197, 1155, 1121, 1102,
1056, 1031, 999 (C–O); 860, 848, 835, 790, 762, 745, 725, 695, 660, 635, 620 (CH ).
Ar
PMR spectrum (δ, ppm): 0.89 (CH , t), 1.22-1.60 [(CH ) , m], 1.84 (CH , t), 2.64 (CH , t), 3.89 (CH O, s), 6.40-7.90
3
2 6
2
2
3
(C H and C H , m), 8.12 and 8.26 (HC=N, s and s), 9.95 (CO H, s).
6
3
6
4
2
4-n-Tridecanoyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3h).
Yield 90%, mp 97-98°C,
-1
C H NO . IR spectrum (ν, cm ): 2100-3640 (OH); 3080, 3065, 3040, 3020, 3010 (=CH and CH ); 2955, 2922, 2852
28 37
5
Ar
(CH ); 1748, 1706 (C=O); 1623 (C=N); 1596, 1507, 1466, 1453, 1421, 1398, 1380 (Ar); 1320, 1282, 1240, 1220, 1198, 1155,
Alk
1123, 1110, 1060, 1028, 1003 (C–O); 860, 852, 840, 790, 762, 746, 720, 695, 655, 640, 620 (CH ).
Ar
PMR spectrum (δ, ppm): 0.90 (CH , t), 1.18-1.68 [(CH ) , m], 1.78 (CH , m), 2.64 (CH , m), 3.88 (CH O, s), 6.45-
3
2 9
2
2
3
8.02 (C H and C H , m), 8.10 and 8.25 (HC=N, s and s), 9.94 (CO H, s).
6
3
6
4
2
4-n-Stearoyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3i). Yield 90%, mp 63-64°C, C H NO .
33 47
5
-1
IR spectrum (ν, cm ): 2120-3660 (OH); 3090, 3080, 3070, 3040, 3007 (=CHand CH ); 2960, 2917, 2850 (CH ); 1762, 1704
Ar
Alk
(C=O); 1624 (C=N); 1597, 1507, 1471, 1421, 1400, 1379, 1354 (Ar); 1313, 1281, 1241, 1220, 1199, 1155, 1122, 1101, 1056,
1032, 1000 (C–O); 860, 845, 835, 800, 790, 762, 719, 693, 640, 620 (CH ).
Ar
PMR spectrum (δ, ppm): 0.90 (CH , t), 1.10-2.12 [(CH ) , m], 2.72 (CH , t), 3.88 (CH O, s), 6.45-8.04 (C H and
3
2 15
2
3
6 3
C H , m), 8.10 and 8.24 (HC=N, s and s), 9.95 (CO H, s).
6
4
2
4-Acryloyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3j). Yield 91%, mp 103-104°C, C H NO .
18 15
5
-1
IR spectrum (ν, cm ): 2050-3650 (OH); 3080, 3070, 3040, 3015 (=CH and CH ); 2960, 2940, 2920, 2880, 2855, 2830
Ar
(CH ); 1753, 1704 (C=O); 1623 (C=N); 1592, 1505, 1463, 1451, 1421, 1397, 1362 (Ar); 1320, 1281, 1241, 1215, 1200, 1160,
Alk
1140, 1122, 1028, 1001 (C–O); 848, 830, 810, 800, 790, 761, 743, 725, 692, 635, 617 (CH ).
Ar
PMR spectrum (δ, ppm): 3.89 (CH O, s), 5.85-6.90 (CH CH , m), 6.40-8.00 (C H and C H , m), 8.12 and 8.26
3
2
6
3
6 4
(HC=N, s and s), 9.94 (CO H, s).
2
4-Metacryloyloxy-3-methoxyphenylmethylen-(2-carboxyphenyl)amine (3k). Yield 90%, mp 140-141°C,
-1
C H NO . IR spectrum (ν, cm ): 2060-3650 (OH); 3090, 3080, 3070, 3040, 3010 (=CHand CH ); 2985, 2960, 2940, 2920,
19 17
5
Ar
2890, 2860, 2830 (CH ); 1734, 1706 (C=O); 1623 (C=N); 1594, 1506, 1466, 1450, 1421, 1397, 1380 (Ar); 1319, 1282, 1241,
Alk
1220, 1203, 1159, 1138, 1029, 1003 (C–O); 870, 846, 825, 803, 785, 762, 745, 725, 692, 650, 640, 618 (CH ).
Ar
208