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ring), 1627 (C]O stretch of amide group), 1533, 1481, 1333 (C– aromatic ring), 2500, 2340, 1658 (C]O stretch of amide group),
N stretch), 1211; 1H-NMR (300 MHz, CDCl3) (ppm): d 3.811 (3H, 1558, 1451, 1309 (C–N stretch), 1246, 1161; 1H-NMR (300 MHz,
s, OCH3), 5.872 (2H, s, NH2), 6.763–6.781 (2H, m, HAr), 7.038– CDCl3) (ppm): d 6.691–6.783 (4H, m, HAr), 7.310–7.401 (3H, m,
7.056 (2H, m, HAr), 7.223 (1H, d, J ¼ 7.5 Hz, HAr), 7.371 (2H, d, J HAr), 7.487–7.538 (1H, m, NH), 7.859 (1H, t, J ¼ 8.1 Hz), 7.957–
¼ 7.8 Hz, HAr), 7.443–7.489 (3H, m, HAr), 7.684 (1H, s, NH); 13C- 8.019 (2H, m, NH2); 13C-NMR: d 116.43, 116.74, 121.42, 124.06,
NMR: d 56.13, 116.33, 117.01, 117.86, 122.12, 127.64, 132.16, 128.50, 132.12, 134.86, 151.06; anal. For C14H11N3SO (269.32)
133.59, 137.61, 151.23, 169.28; anal. for C14H14N2O2 (242.11) calcd; C, 62.43; H, 4.12; N, 15.60; O, 5.94, S, 11.91. Found: C,
calcd; C, 69.41; H, 5.82; N, 11.56; O, 13.21. Found: C, 70.11; H, 62.40; H, 4.10; N, 15.64; O, 5.96; S, 11.90%.
5.57; N, 11.62; O, 12.70%.
2-Amino-N-(p-tolyl)benzamide (3h). Pale yellow solid; mp
142 ꢀC; IR (KBr, cmꢁ1): 3450 (NH stretch), 3321, 3249 (NH2
symm and antisymm stretch), 2981 (C–H stretch of aromatic
ring), 1628 (C]O stretch of amide group), 1549, 1440, 1316 (C–
N stretch), 1198; 1H-NMR (300 MHz, CDCl3) (ppm): d 2.281 (3H,
s, CH3), 5.637 (2H, s, NH2), 6.871–6.890 (2H, m, HAr), 7.218 (2H,
d, J ¼ 7.5 Hz, HAr); 7.385 (1H, d, J ¼ 7.2 Hz, HAr), 7.437–7.481
(3H, m, HAr), 7.882 (1H, s, NH); 13C-NMR: d 20.77, 115.22,
116.33, 117.34, 121.97, 128.41, 132.65, 133.91, 136.53, 150.16,
167.44; anal. for C14H14N2O (226.11) calcd; C, 74.31; H, 6.24; N,
12.38; O, 7.07. Found: C, 73.98; H, 6.11; N, 12.62; O, 7.29%.
2-Amino-N-benzylbenzamide (3i). Cream colored powder;
mp 120 ꢀC; IR (KBr, cmꢁ1): 3472 (NH stretch), 3359, 3304 (NH2
symm and antisymm stretch), 3054 (C–H stretch of aromatic
ring), 1630 (C]O stretch of amide group), 1578, 1541, 1444,
1414, 1324 (C–N stretch), 1269, 1150, 1026; 1H-NMR (300 MHz,
CDCl3) (ppm): d 4.628 (2H, d, J ¼ 5.4 Hz, CH2), 5.569 (2H, br s,
NH2), 6.352 (1H, br s, NH), 6.624–6.720 (2H, m, HAr), 7.197–
7.383 (7H, m, HAr); 13C-NMR: d 43.75, 116.58, 117.34, 127.05,
127.54, 127.79, 128.77, 132.37, 138.46, 149.19, 169.34; anal. for
Acknowledgements
We gratefully acknowledge the nancial support from the
Department of Science Technology and University Grants
Commission for FIST and SAP respectively. One of the
authors Pallavi More thanks the Department of Science
Technology, New Delhi, India for the award of PURSE
fellowship. We also express our thanks to Prof. Dr S. R.
Patil, Department of Chemistry, Shivaji University, Kolhapur
for useful discussion regarding the uorescence spectro-
scopic studies.
References
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14H14N2O (226.27) calcd; C, 74.31; H, 6.24; N, 12.38. Found:
74.30; H, 6.25; N, 12.36%.
2-Amino-N0-phenylbenzohydrazide (3o). Cream colored
powder; mp 171 ꢀC; IR (KBr, cmꢁ1): 3429 (NH stretch), 3335,
3243 (NH2 symm and antisymm stretch), 3021 (C–H stretch of
aromatic ring), 1613 (C]O stretch of amide group), 1587, 1443,
1310 (C–N stretch), 1241, 1155, 1086; 1H-NMR (300 MHz, CDCl3)
(ppm): d 5.537 (2H, br s, NH2), 6.298 (1H, br s, NH), 6.716 (2H, t,
J ¼ 7.2 Hz, HAr), 6.945 (3H, t, J ¼ 7.2 Hz, HAr), 7.248–7.313 (4H,
m, HAr), 7.489–7.517 (1H, d, J ¼ 7.2 Hz, HAr), 7.777 (1H, br s,
NH); 13C-NMR: d 113.19, 113.68, 116.69, 117.46, 121.36, 126.97,
129.25, 133.21, 148.27, 149.26, 169.50; anal. for C13H13N3O
(227.26) calcd; C, 68.70; H, 5.77; N, 18.49. Found: C, 68.73; H,
5.74; N, 18.50%.
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2-Amino-N-(4-uorobenzyl)benzamide (3p). Pale yellow
solid; mp 122 ꢀC; IR (KBr, cmꢁ1): 3474 (NH stretch), 3357, 3315
(NH2 symm and antisymm stretch), 3049 (C–H stretch of
aromatic ring), 1629 (C]O stretch of amide group), 1538, 1303
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1
(C–N stretch), 1219, 1159; H-NMR (300 MHz, CDCl3) (ppm): d
4.589 (2H, d, J ¼ 7.5 Hz, CH2), 6.383 (1H, br s, NH), 6.631–6.743
(2H, m, HAr), 7.023–7.080 (2H, m, NH2), 7.209–7.359 (6H, m,
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127.05, 129.39, 129.49, 132.51, 134.11, 148.86, 160.60, 163.86,
169.20; anal. for C14H13N2FO (244.26) calcd; C, 68.84; H, 5.36; F,
7.78; N, 11.47. Found: C, 68.80; H, 5.38; F, 7.80; N, 11.50%.
2-Amino-N-(1,3-benzothiazol-2-yl)benzamide (3q). White
solid; mp 166 ꢀC; IR (KBr, cmꢁ1): 3730 (NH stretch), 3444, 3419
(NH2 symm and antisymm stretch), 3054, 2917 (C–H stretch of
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63046 | RSC Adv., 2014, 4, 63039–63047
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