Aldehydes and Pyrazolones
1267
3b. Anal. calcd. for C27H23ClN4O2:C, 68.71; H, 4.91; N, 11.87. Found: C,
68.55; H, 4.48; 12.05. IR (KBr): nmax: 3450, 3060, 2925, 1620, 1560, 1505,
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1441, 1367, 1299, 844, 757 cm21. H NMR (DMSO): d: 2.24 (s, 6H, CH3),
5.03 (s, IH, CH), 7.23–7.25 (m, 2H, ArH), 7.40–7.42 (m, 8H, ArH), 7.73–
7.75 (m, 4H, ArH).
3c. Anal. calcd. for C27H23ClN4O2: C, 68.71; H, 4.91; N, 11.87. Found: C,
68.46; H, 5.05; 11.62. IR (KBr): nmax: 3426, 3100, 2987, 1600, 1472, 1429,
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1366, 1296, 1100, 1074, 870, 745 cm21. H NMR (DMSO): d: 2.33 (s, 6H,
CH3), 4.99 (s, 1H, CH), 7.24–7.31 (m, 5H, ArH), 7.33–7.35 (m, 1H, ArH),
7.43–7.47 (m, 4H, ArH), 7.70–7.72 (m, 4H, ArH).
3f. Anal. calcd. for C27H23N5O4: C, 67.21; H, 4.80; N, 14.51. Found: C,
67.15; H, 4.91; 14.36. IR (KBr): nmax: 3441, 3048, 2951, 1642, 1559, 1439,
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1352, 1294, 1246, 880, 828, 736 cm21. H NMR (DMSO): d: 2.25 (s, 6H,
CH3), 5.44 (s, 1H, CH), 7.22–7.29 (m, 2H, ArH), 7.42–7.49 (m, 5H, ArH),
7.63–7.73 (m, 7H, ArH).
3l. Anal. calcd. for C21H20N4O2: C, 69.98; H, 5.59; N, 15.55. Found C,
69.73; H, 5.47; 15.38. IR (KBr): nmax: 3440, 3059, 2884, 2781, 1577, 1497,
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1406, 1363, 1312, 1179, 904, 794, 751, 686 cm21. H NMR (DMSO): d:
2.23 (s, 6H, CH3), 3.24 (s, 2H, CH2), 7.23–7.25 (m, 2H, ArH), 7.42–7.46
(m, 4H, ArH), 7.70–7.72 (m, 4H, ArH).
3m. Anal. calcd. for C24H26N4O2: C, 71.62; H, 6.51; N, 13.92. Found: C,
71.54; H, 6.62; 13.85. IR (KBr): nmax: 3428, 3061, 2959, 2733, 1585, 1499,
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1420, 1291, 1182, 1122, 1027, 901, 791, 750, 638 cm21. H NMR (DMSO):
d: 0.84 [S, 6H, CH(CH3)2], 2.21 (s, 6H, CH3), 2.50–2.64 [m, 1H,
CH(CH3)2], 2.99–3.01 [d, 1H, CHCH(CH3)2], 7.22–7.25 (m, 2H, ArH),
7.42–7.46 (m, 4H, ArH), 7.70–7.72 (m, 4H, ArH).
3n. Anal. calcd. for C15H16N4O2: C, 63.37; H, 5.67; N, 19.71. Found: C,
63.54; H, 5.42; N, 20.05. IR (KBr): nmax: 3415, 1606, 1530, 1491, 1388, 1143,
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823, 783, 723 cm21. H NMR (DMSO): d: 2.08 (s, 6H, CH3), 4.82 (m, 1H,
CH), 7.13–7.14 (d, 3H, ArH), 7.19–7.23 (m, 2H, ArH).
3o. Anal. calcd. for C15H15ClN4O2: C, 56.52; H, 4.74; N, 17.58. Found:
C, 56.41; H, 4.42; N, 17.36 IR (KBr): nmax: 3437, 1614, 1488, 1388, 1094,
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757 cm21. H NMR (DMSO): d: 2.08 (s, 6H, CH3), 4.82 (m, 1H, CH), 7.12
(s, 2H, ArH), 7.27 (m, 2H, ArH).
3p. Anal. calcd. for C15H16N4O3: C, 59.99; H, 5.37; N, 18.66. Found: C,
59.80; H, 5.42; N, 18.36. IR (KBr): nmax: 3266, 1561, 1514, 1466, 1400, 1174,
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872, 786, 731 cm21. H NMR (DMSO): d: 2.06 (s, 6H, CH3), 4.71 (m, 1H,
CH), 6.58–6.60 (d, 2H, ArH), 6.90–6.92 (d, 2H, ArH).
3q. Anal. calcd. for C15H15N5O4: C, 54.71; H, 4.59; N, 21.27. Found: C,
54.50; H, 4.45; N, 20.98. IR (KBr): nmax: 3419, 2961, 1599, 1447, 1390, 1182,
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837, 795, 764 cm21. H NMR (DMSO): d: 2.11 (s, 6H, CH3), 4.99 (ms, 1H,
CH), 7.54–7.57 (d, 2H, ArH), 7.96 (s, 1H, ArH), 8.03–8.04 (s, 1H, ArH).
3r. Anal. calcd. for C15H15N5O4: C, 54.71; H, 4.59; N, 21.27. Found: C,
54.52; H, 4.43; N, 21.05. IR (KBr): nmax: 3419, 2961, 1603, 1510, 1442, 1346,