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Chauhan, Singh, and Geetanjali
(80), 103 (40), 43 (83). Anal. calcd. for C11H12N2O4: C, 55.92; H, 5.12; N,
11.85. Found: C, 55.93; H, 5.14; N, 11.84.
4-Methoxycarbonyl-2-nitro-N-phenylaniline(3r). IR(KBr):3431, 1722,
1
1664, 1621, 1566, 1525, 1435, 1356, 1114, 844, 754. H NMR (CDCl3):
3.97 (s, 3H, OCH3), 6.99 (d, 1H, 6-H, J ¼ 7.99 Hz), 7.26–7.35 (m, 5H, N-
phenyl protons), 7.49 (d, 1H, 5-H, J ¼ 7.98 Hz), 8.01 (s, 1H, 3-H), 8.19
(bs, 1H, NH). MS m/z (% base): 272 (Mþ, 85), 256 (12), 255 (20), 241
(25), 213 (9). Anal. calcd. for C14H12N2O4: C, 61.76; H, 4.44; N, 10.28.
Found: C, 61.75; H, 4.43; N, 10.26.
4-Methoxycarbonyl-N-(40-methoxyphenyl)-2-nitroaniline (3s). IR (KBr):
3343, 2925, 1722, 1627, 1567, 1515, 1432, 1357, 1286, 1214, 1125,
1
819, 757. H NMR (CDCl3): 3.90 (s, 3H, OCH3), 3.95 (s, 3H, OCH3),
6.90 (d, 1H, 6-H, J ¼ 8.75 Hz), 6.92–7.20 (m, 4H, 20, 30, 50 & 60-H),
8.00 (d, 1H, 5-H, J ¼ 8 Hz), 8.18 (bs, 1H, NH), 8.95 (s, 1H, 3-H). MS
m/z (% base): 302 (Mþ, 5), 301 (76), 287 (5), 286 (22), 259 (15), 271 (5),
195 (10), 237 (12), 182 (14), 91 (7), 77 (7), 58 (35), 43 (100). Anal. calcd.
for C15H15N2O5: C, 59.40; H, 4.98; N, 9.23. Found: C, 59.38; H, 4.97;
N, 9.25.
N-Cyclohexyl-4-methoxycarbonyl-2-nitroaniline (3t). IR (KBr): 3337,
2930, 1713, 1623, 1568, 1525, 1438, 1364, 1270, 1218, 1152, 972, 760.
1H NMR (CDCl3): 1.20–2.40 (m, 11H, C6H11), 4.00 (s, 3H, OCH3),
7.00 (d, 1H, 6-H, J ¼ 8 Hz), 8.10 (bs, 1H, NH), 8.15 (d, 1H, 5-H,
J ¼ 8 Hz), 9.00 (d, 1H, 3-H, J ¼ 1.2 Hz). MS m/z (% base): 278 (Mþ,
6), 277 (21), 261 (7), 235 (63), 195 (14), 161 (26), 119 (8), 58 (28), 56
(25), 43 (100). Anal. calcd. for C14H18N2O4: C, 60.42; H, 6.51; N, 10.06.
Found: C, 60.42; H, 6.52; N, 10.04.
N-Benzyl-4-methoxycarbonyl-2-nitroaniline (3v). IR (KBr): 3368,
2927, 1714, 1624, 1566, 1530, 1438, 1354, 1297, 1250, 1221, 1192, 1116,
1
969, 757. H NMR (CDCl3): 3.95 (s, 3H, OCH3), 4.70 (d, 2H, NCH2,
J ¼ 5.8 Hz), 6.95 (d, 1H, 6-H, J ¼ 8.0 Hz), 7.40–7.45 (m, 5H, Ar-H), 8.10
(d, 1H, 5-H, J ¼ 8 Hz), 8.15 (bs, 1H, NH), 9.00 (s, 1H, 3-H). MS m/z (%
base): 286 (Mþ, 29), 285 (100), 237 (45), 236 (63), 208 (90), 179 (32), 105
(100), 91 (100), 77 (44). Anal. calcd. for C15H14N2O4: C, 62.93; H, 4.92;
N, 9.78. Found: C, 62.92; H, 4.93; N, 9.80.
N-(40-Bromophenyl)-4-methoxycarbonyl-2-nitroaniline (3w). IR (KBr):
3313, 3097, 2942, 1716, 1617, 1584, 1564, 1523, 1433, 1354, 1283, 1213,
1148, 1071, 963, 754. 1H NMR (CDCl3): 4.00 (s, 3H, OCH3), 6.90 (d, 1H,
6-H, J ¼ 8.0 Hz), 7.20–7.70 (m, 4H, 20, 30, 50, 60-H), 8.10 (d, 1H, 5-H,
J ¼ 8.1 Hz), 8.18 (bs, 1H, NH), 9.00 (s, 1H, 3-H). MS m/z (% base):
353 (M þ 2, 100), 351 (Mþ, 100), 271 (24), 334 (15), 318 (37), 245 (25),
226 (33), 194 (81), 166 (100), 139 (52). Anal. calcd. for C14H11N2O4Br: C,
47.88; H, 3.15; N, 7.97. Found: C, 47.86; H, 3.14; N, 7.95.