164 Lee et al.
1509; EI-MS (m/z, %): 277 (M+, 6), 259 (100),
244 (52), 107 (23), 79(29); HRMS (EI) calcd for
C14H12ClNO3 277.0506, found 277.0507.
20.85; IR (KBr) ν (cm−1): 3414, 3045, 3015, 2961,
1647, 1607; EI-MS (m/z, %): 257 (M+, 15), 239 (3),
135 (100), 107 (6), 92 (7), 77 (12).
N-(5-Fluoro-2-hydroxyphenyl)benzamide
(16)
N-(4-Chloro-2-hydroxy-4-methylphenyl)benza-
[27]. Yield 76%, pale beige solid, mp 205–206◦C;
mide (12) [25]. Yield 56%, white solid, mp 215–
1
1
216◦C; TLC (30% ethyl acetate/hexane) R 0.60; H
TLC (30% ethyl acetate/hexane) R 0.24; H NMR
f
f
(400 MHz, DMSO-d6) δ: 9.89 (s, 1H), 9.45 (s, 1H),
7.96 (d, J = 6.8 Hz, 2H), 7.72 (dd, J = 10.4, 2.8 Hz,
1H), 7.62–7.51 (m, 3H), 6.92–6.83 (m, 2H); 13C NMR
(100 MHz, DMSO-d6) δ: 165.58, 156.38, 154.07,
145.43, 145.41, 134.52, 132.32, 129.02, 127.91,
127.12, 127.00, 116.28, 116.19, 111.61, 111.38,
110.41, 110.14; IR (KBr) ν (cm−1): 3418, 3109, 3064,
2991, 1653, 1539; EI-MS (m/z, %): 231 (M+, 12), 213
(5), 105 (100), 77 (39), 51 (8).
NMR (400 MHz, DMSO-d6) δ: 9.58 (s, 1H), 9.56 (s,
1H), 7.99 (d, J = 8.4 Hz, 2H), 7.59 (d, J = 8.4 Hz,
2H), 7.45 (d, J = 7.6 Hz, 1H), 6.73 (s, 1H), 6.64 (d,
J = 7.6 Hz, 1H), 2.22 (s, 3H); 13C NMR (100 MHz,
DMSO-d6) δ: 164.18, 149.60, 136.29, 135.37, 133.18,
129.46, 128.43, 124.58, 122.92, 119.55, 116.60, 20.67;
IR (KBr) ν (cm−1): 3417, 3075, 3048, 2924, 1640,
1540; EI-MS (m/z, %): 261 (M+, 25), 243 (4), 139
(100), 111 (24), 75 (6).
N-(5-Fluoro-2-hydroxyphenyl)-4-methoxybenza-
N-(2-Hydroxy-5-methoxyphenyl)benzamide (13)
[26]. Yield 78%, white solid, mp 167–168◦C; TLC
mide (17). Yield 52%, pale beige solid, mp 202–
1
203◦C; TLC (40% ethyl acetate/hexane) R 0.32; H
1
(30% ethyl acetate/hexane) R 0.29; H NMR (400
f
f
NMR (400 MHz, DMSO-d6) δ: 9.86 (s, 1H), 9.33 (s,
1H), 7.94 (d, J = 8.8 Hz, 2H), 7.70 (dd, J = 10.8,
3.2 Hz, 1H), 7.07 (d, J = 8.8 Hz, 2H), 6.90–6.80
(m, 2H), 3.83 (s, 3H); 13C NMR (100 MHz, DMSO-
d6) δ: 164.60, 162.10, 156.02, 153.70, 144.65, 144.63,
129.38, 127.01, 126.90, 126.10, 115.92, 115.82,
113.80, 110.78, 110.54, 109.55, 109.28, 55.41; IR
(KBr) ν (cm−1): 3414, 3102, 3022, 2975, 1654, 1610;
EI-MS (m/z, %): 243 (M+– 18, 100), 228 (30), 200
(37), 121 (4), 63 (4); HRMS (EI) calcd for C14H12FNO3
261.0801, found 261.0804.
MHz, DMSO-d6) δ: 9.50 (s, 1H), 9.31 (s, 1H), 7.97
(d, J = 7.6 Hz, 2H), 7.61–7.51 (m, 3H), 7.42 (d, J =
2.8 Hz, 1H), 6.85 (d, J = 8.8 Hz, 1H), 6.65 (dd, J =
9.6, 2.8 Hz, 1H), 3.68 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ: 166.88, 153.73, 142.15, 133.44, 132.46,
128.95, 127.33, 126.23, 119.79, 112.50, 107.61, 55.86;
IR (KBr) ν (cm−1): 3404, 3089, 3045, 2985, 1650,
1540; EI-MS (m/z, %): 243 (M+, 22), 225 (7), 210
(5), 138 (14), 105 (100), 77 (35), 51 (6).
N - (2 - Hydroxy - 5 - methoxyphenyl) - 4 - methoxy-
benzamide (14). Yield 43%, white solid, mp 174–
1
175◦C; TLC (40% ethyl acetate/hexane) R 0.36; H
4-Chloro-N-(5-fluoro-2-hydroxyphenyl)benza-
f
NMR (400 MHz, DMSO-d6) δ: 9.40 (s, 1H), 9.28 (s,
1H), 7.95 (d, J = 8.8 Hz, 2H), 7.39 (d, J = 3.2
Hz, 1H), 7.07 (d, J = 8.8 Hz, 2H), 6.84 (d, J =
8.8 Hz, 1H), 6.63 (dd, J = 8.8, 3.3 Hz, 1H), 3.83
(s, 3H), 3.68 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ: 166.44, 163.14, 153.66, 142.59, 129.30, 126.26,
125.47, 120.18, 112.50, 107.70, 55.86, 55.54; IR
(KBr) ν (cm−1): 3384, 3095, 3008, 2948, 1637, 1603;
EI-MS (m/z, %): 273 (M+, 8), 255 (38), 240 (21), 135
(100), 92 (7), 77 (14); HRMS (EI) calcd for C15H15NO4
273.1005, found 273.0999.
mide (18). Yield 66%, pale pink solid, mp 209–
1
210◦C; TLC (30% ethyl acetate/hexane) R 0.32; H
f
NMR (400 MHz, DMSO-d6) δ: 10.17 (s, 1H), 9.62 (s,
1H), 7.99 (d, J = 8.8 Hz, 2H), 7.60–7.57 (m, 2H), 7.53
(t, J = 7.2 Hz, 1H), 6.73 (dd, J = 10.4, 2.4 Hz, 1H),
6.68 (td, J = 8.8, 3.2 Hz, 1H); 13C NMR (100 MHz,
DMSO-d6) δ: 164.21, 155.92, 153.60, 145.28, 145.26,
136.62, 132.92, 129.49, 128.57, 126.44, 126.33,
115.95, 115.86, 111.45, 111.22, 110.38, 110.11; IR
(KBr) ν (cm−1): 3400, 3182, 3048, 2988, 1650, 1543;
EI-MS (m/z,%): 265 (M+, 9), 247 (9), 139 (100),
111 (27), 75 (9); HRMS (EI) calcd for C13H9ClFNO2
265.0306, found 265.0307.
4-Chloro-N-(2-hydroxy-5-methoxyphenyl)benza-
mide (15). Yield 50%, white solid, mp 211–212◦C;
1
TLC (30% ethyl acetate/hexane) R 0.44; H NMR
N-(4-Fluoro-2-hydroxyphenyl)benzamide
(19)
f
(400 MHz, DMSO-d6) δ: 9.56 (s, 1H), 9.24 (s, 1H),
7.98 (d, J = 8.4 Hz, 2H), 7.60 (d, J = 8.8 Hz, 2H), 7.35
(d, J = 2.4 Hz, 1H), 6.84 (d, J = 8.8 Hz, 1H), 6.65 (dd,
J = 8.8, 2.8 Hz, 1H), 3.68 (s, 3H); 13C NMR (100 MHz,
DMSO-d6) δ: 164.16, 151.94, 142.93, 136.49, 133.06,
129.45, 128.54, 126.15, 116.27, 110.81, 109.61, 55.37;
IR (KBr) ν (cm−1): 3280, 3206, 3038, 2964, 1633,
[28]. Yield 54%, pale beige solid, mp 218–219◦C;
1
TLC (30% ethyl acetate/hexane) R 0.39; H NMR
f
(400 MHz, DMSO-d6) δ: 10.22 (s, 1H), 9.55 (s, 1H),
7.98 (d, J = 8.0 Hz, 2H), 7.60–7.49 (m, 4H), 6.74
(dd, J = 9.6, 2.8 Hz, 1H), 6.89 (td, J = 8.8, 2.4
Hz, 1H); 13C NMR (100 MHz, DMSO-d6) δ: 165.77,
161.52, 159.12, 152.44, 152.03, 134.66, 132.06,
Heteroatom Chemistry DOI 10.1002/hc