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Z. LI ET AL.
8.75 (d, J ¼ 7.50 Hz, 1H, Ar-H), 9.17 (s, 1H, NH), 12.94 (1H, COOH) ppm. HRMS:
found 241.1102; calcd. 241.1103 for C15H15NO2.
2-((2,3-Dimethylphenyl)amino)benzoic acid (3b). Mp 226–228 ꢀC (lit.[7]
1
228–230 ꢀC); FT-IR (KBr): nN-H 3314, nC¼O 1653, 1577 cmꢁ1; H NMR (DMSO-
d6, 500 MHz): d ¼ 2.10 (s, 3H, CH3), 2.29 (s, 3H, CH3), 6.70 (t, J ¼ 8.00 Hz, 2H,
Ar-H), 7.02–7.13 (m, 3H, Ar-H), 7.30 (t, J ¼ 8.00 Hz, 1H, Ar-H), 7.80 (dd,
J ¼ 8.00 Hz, 1.50 Hz, 1H, Ar-H), 9.46 (s, 1H, NH), 13.01 (s, 1H, COOH) ppm.
HRMS: found 241.1106; calcd. 241.1103 for C15H15NO2.
2-(Mesitylamino)benzoic acid (3c). Mp 229–230 ꢀC; FT-IR (KBr): nN-H
3350, nC¼O 1653, 1573 cmꢁ1
;
1H NMR (DMSO-d6, 500 MHz): d ¼ 2.07 (s, 6H,
CH3), 2.27 (s, 3H, CH3), 6.06 (d, J ¼ 8.00 Hz, 1H, Ar-H), 6.62 (t, J ¼ 7.50 Hz, 1H,
Ar-H), 6.99 (s, 2H, Ar-H), 7.23 (t, J ¼ 8.00 Hz, 1H, Ar-H), 7.86 (dd, J ¼ 8.00 Hz,
1.50 Hz, 1H, Ar-H), 9.07 (s, 1H, NH), 12.87 (s, 1H, COOH) ppm. HRMS: found
255.1265; calcd. 255.1259 for C16H17NO2.
2-((2-Ethyl-6-methylphenyl)amino)benzoic acid (3d). Mp 153–155 ꢀC;
1
FT-IR (KBr): nN-H 3343, nC¼O 1653, 1573 cmꢁ1; H NMR (DMSO-d6, 500 MHz):
d ¼ 1.06 (t, J ¼ 7.50 Hz, 3H, CH3), 2.10 (s, 3H, CH3), 2.47 (t, J ¼ 7.50 Hz, 2H,
CH2), 6.08 (d, J ¼ 8.50 Hz, 1H, Ar-H), 6.63 (t, J ¼ 7.50 Hz, 1H, Ar-H), 7.18–7.21
(m, 3H, Ar-H), 7.25 (t, J ¼ 8.00 Hz, 1H, Ar-H), 7.87 (dd, J ¼ 8.00 Hz, 1.50 Hz, 1H,
Ar-H), 9.22 (s, 1H, NH), 12.92 (s, 1H, COOH) ppm. 13C NMR (DMSO-d6,
500 MHz): d170.43, 149.88, 141.99, 136.41, 136.36, 134.57, 131.83, 128.67, 127.10,
127.00, 115.73, 112.07, 110.35, 24.61, 18.02, 15.09. HRMS: found 255.1262; calcd.
255.1259 for C16H17NO2.
2-((2,6-Diethylphenyl)amino)benzoic acid (3e). Mp 177–178 ꢀC; FT-IR
(KBr): nN-H 3350, nC¼O 1657, 1577 cmꢁ1
;
1H NMR (DMSO-d6, 500 MHz):
d ¼ 1.06 (t, J ¼ 7.50 Hz, 6H, CH3), 2.43–2.48 (m, 4H, CH2), 6.09 (d, J ¼ 8.50 Hz,
1H, Ar-H), 6.62 (t, J ¼ 7.50 Hz, 1H, Ar-H), 7.20–7.26 (m, 4H, Ar-H), 7.86 (dd,
J ¼ 8.00 Hz, 1.50 Hz, 1H, Ar-H), 9.24 (s, 1H, NH), 12.92 (s, 1H, COOH) ppm. 13C
NMR (DMSO-d6, 500 MHz): d 170.30, 150.16, 142.08, 135.58, 134.32, 131.61,
127.15, 126.88, 115.45, 111.95, 110.07, 24.34, 14.81. HRMS: found 269.1418; calcd.
269.1416 for C17H19NO2.
2-((2,6-Diisopropylphenyl)amino)benzoic acid (3f). Mp 217–219 ꢀC;
1
FT-IR (KBr): nN-H 3340, nC¼O 1661, 1574 cmꢁ1; H NMR (DMSO-d6, 500 MHz):
d ¼ 1.07 (d, J ¼ 7.00 Hz, 6H, CH3), 1.10 (d, J ¼ 6.50 Hz, 6H, CH3), 2.97–3.03 (m,
2H, CH), 6.07 (d, J ¼ 8.50 Hz, 1H, Ar-H), 6.61 (t, J ¼ 7.50 Hz, 1H, Ar-H),
7.23–7.27 (m, 3H, Ar-H), 7.33 (t, J ¼ 8.00 Hz, 1H, Ar-H), 7.85 (dd, J ¼ 8.00 Hz,
1.50 Hz, 1H, ArH), 9.12 (s, 1H, NH), 12.92 (s, 1H, COOH) ppm. 13C NMR
(DMSO-d6, 500 MHz): d 170.30, 150.86, 146.78, 134.29, 133.96, 131.61, 127.68,
123.82, 115.37, 112.10, 109.85, 27.98, 24.33, 22.67. HRMS: found 297.1736; calcd.
297.1729 for C19H23NO2.
2-((2,4,6-Trichlorophenyl)amino)benzoic acid (3g). Mp 238–240 ꢀC;
1
FT-IR (KBr): nN-H 3300, nC¼O 1662, 1580 cmꢁ1; H NMR (DMSO-d6, 500 MHz):
d ¼ 6.24 (d, J ¼ 8.50 Hz, 1H, ArH), 6.80 (t, J ¼ 7.50 Hz, 1H, ArH), 7.32 (t,
J ¼ 8.00 Hz, 1H, ArH), 7.88 (s, 1H, ArH), 7.90 (dd, J ¼ 8.00 Hz, 1.50 Hz, 2H,