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acetate in hexane) = 0.30. H NMR (400 MHz, CDCl3): δ = 12.69 (s,
2930, 1942, 1633, 1615, 1579, 1519, 1472, 1427, 1339, 1251, 1219,
1159, 1119, 1085, 953, 927, 845, 758, 748, 721, 658, 638 cm–1. HRMS
(EI+): calcd. for C14H11NO4 [M]+ 257.0688; found 257.0682.
(5-Chloro-2-hydroxyphenyl)(pyridin-3-yl)methanone (4.1):[16]
1 H, Ar-OH), 7.46–7.42 (m, 1 H, Ar-H), 7.26–7.20 (m, 2 H, Ar-H) 7.05–
6.98 (m, 2 H, Ar-H), 6.46 (d, J = 2.3 Hz, 1 H, Ar-H), 6.33 (dd, J = 9.2,
2.3 Hz, 1 H, Ar-H), 3.83 (s, 3 H, OCH3), 3.77 (s, 3 H, OCH3) ppm. 13C
NMR (125 MHz, CDCl3): δ = 200.03, 166.28, 165.82, 156.29, 135.36,
131.51, 128.73, 127.88, 120.41, 114.31, 111.32, 107.52, 100.55, 55.62,
Yellow solid (107 mg, 92 %), m.p. 138–140 °C. Rf (10 % ethyl acetate
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in hexane) = 0.20. H NMR (400 MHz, CDCl3): δ = 11.73 (s, 1 H, Ar-
55.58 ppm. IR (KBr): ν = 3021, 2944, 2841, 1604, 1488, 1463, 1436,
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OH), 8.92 (d, J = 2.3 Hz, 1 H, Ar-H), 8.85 (dd, J = 4.8, 1.8 Hz, 1 H, Ar-
H), 8.0 (td, J = 8.2, 1.8 Hz, 1 H, Ar-H), 7.51–7.47 (m, 3 H, Ar-H), 7.06–
7.05 (m, 1 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 198.42,
161.73, 152.94, 149.70, 136.88, 136.44, 132.99, 131.81, 123.84,
1378, 1258, 1204, 1121, 1020, 920, 814, 759 cm–1. HRMS (EI+): calcd.
for C15H14O4 [M]+ 258.0892; found 258.0892.
(3-Hydroxy-4-methoxyphenyl)(2-hydroxy-3,4,5-trimethoxy-
phenyl)methanone (3.27):[15] Yellow solid (123 mg, 73 %), m.p.
127–129 °C. Rf (10 % ethyl acetate in hexane) = 0.20. 1H NMR
(400 MHz, CDCl3): δ = 12.13 (s, 1 H, Ar-OH), 7.31 (d, J = 2.3 Hz, 1 H,
Ar-H), 7.28–7.25 (m, 1 H, Ar-H), 6.94 (d, J = 8.2 Hz, 1 H, Ar-H), 6.91
(s, 1 H, Ar-H), 5.77 (s, 1 H, Ar-OH), 4.05 (s, 3 H, OCH3), 3.98 (s, 3 H,
OCH3), 3.96 (s, 3 H, OCH3), 3.73 (s, 3 H, OCH3) ppm. 13C NMR
(100 MHz, CDCl3): δ = 198.98, 153.46, 149.76, 149.46, 145.41, 144.62,
141.48, 131.32, 122.49, 115.52, 113.73, 110.53, 109.86, 61.30, 61.10,
123.45, 120.38, 119.49 ppm. IR (KBr): ν = 2922, 2848, 2578, 1647,
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1593, 1496, 1432, 1289, 1253, 1197, 1117, 1047, 966, 885, 811 cm–
1. HRMS (EI+): calcd. for C12H8ClNO2 [M]+ 233.0244; found 233.0241.
(5-Bromo-2-hydroxyphenyl)(pyridin-3-yl)methanone (4.2):[16]
Yellow solid (118 mg, 85 %), m.p. 146–148 °C. Rf (10 % ethyl acetate
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in hexane) = 0.20. H NMR (400 MHz, CDCl3): δ = 11.76 (s, 1 H, Ar-
OH), 8.92 (d, J = 1.8 Hz, 1 H, Ar-H), 8.85 (dd, J = 5.0, 1.8 Hz, 1 H, Ar-
H), 8.01–7.99 (m, 1 H, Ar-H), 7.64–7.61 (m, 2 H, Ar-H), 7.50 (dd, J =
7.8, 5.0 Hz, 1 H, Ar-H), 7.02 (d, J = 8.7 Hz, 1 H, Ar-H) ppm. 13C NMR
(100 MHz, CDCl3): δ = 198.37, 162.19, 152.97, 149.72, 139.66, 136.46,
56.64, 56.09 ppm. IR (KBr): ν = 3365, 2935, 2838, 1572, 1491, 1449,
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1349, 1274, 1208, 1132, 1095, 1044, 1020, 925, 896, 797, 761 cm–1
HRMS (EI+): calcd. for C17H18O7 [M]+ 334.1053; found 334.1057.
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134.83, 132.99, 123.49, 120.77, 120.15, 110.66 ppm. IR (KBr): ν =
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2922, 2573, 1648, 1591, 1431, 1288, 1254, 1196, 1047, 960, 811, 761,
622, 522 cm–1. HRMS (EI+): calcd. for C12H8BrNO2 [M]+ 276.9738;
found 276.9739.
4-(2-Hydroxy-5-nitrobenzoyl)benzaldehyde (3.28): White solid
(99 mg, 73 %), m.p. 156–158 °C. Rf (30 % ethyl acetate in hexane) =
0.20. H NMR (400 MHz, CDCl3): δ = 12.48 (s, 1 H, Ar-OH), 10.17 (s,
1 H, CHO), 8.51 (d, J = 2.7 Hz, 1 H, Ar-H), 8.42 (dd, J = 9.1, 2.7 Hz, 1
H, Ar-H), 8.10 (d, J = 8.7 Hz, 2 H, Ar-H), 7.86 (d, J = 8.2 Hz, 2 H, Ar-
H), 7.22 (d, J = 9.6 Hz, 1 H, Ar-H) ppm. 13C NMR (100 MHz, CDCl3):
δ = 199.73, 191.11, 167.92, 141.02, 139.58, 138.90, 131.41, 129.94,
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(3,5-Dichloro-2-hydroxyphenyl)(pyridin-3-yl)methanone
(4.3):[16] Yellow solid (56 mg, 42 %), m.p. 122–124 °C. Rf (10 % ethyl
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acetate in hexane) = 0.20. H NMR (400 MHz, CDCl3): δ = 12.21 (s,
1 H, Ar-OH), 8.92 (d, J = 2.0 Hz, 1 H, Ar-H), 8.87 (dd, J = 4.8, 1.6 Hz,
1 H, Ar-H), 8.01 (dt, J = 8.0, 2.0 Hz, 1 H, Ar-H), 7.64 (d, J = 2.5 Hz, 1
H, Ar-H), 7.52 (dd, J = 8.0, 7.8 Hz, 1 H, Ar-H), 7.45 (d, J = 2.5 Hz, 1
H, Ar-H) ppm. 13C NMR (125 MHz, CDCl3): δ = 198.19, 157.46, 153.28,
149.70, 136.57, 136.41, 132.56, 130.43, 124.38, 123.66, 123.58,
129.60, 129.28, 119.85, 117.61 ppm. IR (KBr): ν = 3428, 2864, 1705,
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1614, 1470, 1343, 1328, 1205, 1091, 837 cm–1. HRMS (EI+): calcd. for
C
14H9NO5 [M]+ 271.0481; found 271.0471.
4-(2-Hydroxy-3-methoxybenzoyl)benzaldehyde (3.29): Yellow
solid (96 mg, 75 %), m.p. 112–114 °C. Rf (10 % ethyl acetate in hex-
ane) = 0.17. 1H NMR (400 MHz, CDCl3): δ = 12.04 (s, 1 H, Ar-OH),
10.12 (s, 1 H, CHO), 8.01 (d, J = 8.2 Hz, 2 H, Ar-H), 7.82 (d, J = 8.2 Hz,
2 H, Ar-H), 7.12 (d, J = 8.2 Hz, 1 H, Ar-H), 7.08 (dd, J = 8.2, 1.4 Hz, 1
H, Ar-H), 6.86–6.82 (m, 1 H, Ar-H), 3.95 (s, 3 H, OCH3) ppm. 13C NMR
(100 MHz, CDCl3): δ = 200.75, 191.45, 153.51, 149.03, 142.88, 138.12,
129.49, 129.45, 124.33, 118.91, 118.35, 117.41, 56.26 ppm. IR (KBr):
119.98 ppm. IR (KBr): ν = 3435, 3085, 2923, 1657, 1591, 1463,
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1406, 1318, 1263, 1239, 1179, 1159, 1051, 979, 873, 832, 764, 707,
670 cm–1. HRMS (EI+): calcd. for C12H7Cl2NO2 [M]+ 266.9854; found
266.9851.
(2-Hydroxyphenyl)(pyridin-3-yl)methanone (4.4):[16] Yellow solid
(94 mg, 94 %), m.p. 68–70 °C. Rf (10 % ethyl acetate in hexane) =
0.15. 1H NMR (400 MHz, CDCl3): δ = 11.86 (s, 1 H, Ar-OH), 8.92 (d,
J = 1.8 Hz, 1 H, Ar-H), 8.82 (dd, J = 4.8, 1.9 Hz, 1 H, Ar-H), 8.01 (td,
J = 7.8, 1.8 Hz, 1 H, Ar-H), 7.57–7.53 (m, 2 H, Ar-H), 7.48 (dd, J = 7.4,
5.0 Hz, 1 H, Ar-H), 7.10 (d, J = 8.2 Hz, 1 H, Ar-H), 6.93–6.89 (m, 1 H,
Ar-H) ppm. 13C NMR (100 MHz, CDCl3): δ = 199.29, 163.26, 152.43,
149.71, 137.03, 136.58, 133.63, 133.07, 123.36, 119.07, 118.88,
ν = 3416, 2937, 2840, 1705, 1625, 1607, 1453, 1438, 1336, 1304,
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1256, 1205, 1075, 980, 835, 787, 751 cm–1. HRMS (EI+): calcd. for
C15H12O4 [M]+ 256.0736; found 256.0734.
(2-Hydroxy-4-methoxyphenyl)(o-tolyl)methanone (3.30): Col-
ourless liquid (88 mg, 73 %). Rf (10 % ethyl acetate in hexane) =
0.72. 1H NMR (400 MHz, CDCl3): δ = 12.79 (s, 1 H, Ar-OH), 7.40–7.36
(m, 1 H, Ar-H), 7.29–7.23 (m, 3 H, Ar-H), 7.18 (d, J = 9.2 Hz, 1 H, Ar-
H), 6.50 (d, J = 2.3 Hz, 1 H, Ar-H), 6.36–6.33 (m, 1 H, Ar-H), 3.85 (s,
3 H, OCH3), 2.30 (s, 3 H, CH3) ppm. 13C NMR (100 MHz, CDCl3): δ =
202.42, 166.52, 166.22, 138.08, 135.26, 130.75, 129.82, 127.24,
118.68 ppm. IR (KBr): ν = 3047, 2926, 1627, 1608, 1584, 1484, 1338,
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1308, 1249, 1148, 935, 160, 709, 658 cm–1. HRMS (EI+): calcd. for
C12H9NO2 [M]+ 199.0633; found 199.0623.
N-[2-(4-Methoxybenzoyl)phenyl]-4-methylbenzenesulfonamide
(5.1): Colourless solid (158 mg, 83 %), m.p. 128–130 °C. Rf (20 %
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ethyl acetate in hexane) = 0.3. H NMR (400 MHz, CDCl3): δ = 9.67
125.29, 114.02, 107.68, 100.84, 55.64, 19.48 ppm. IR (neat): ν = 3018,
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(s, 1 H, Ar-NH), 7.77 (d, J = 7.3 Hz, 1 H, Ar-H), 7.52–7.47 (m, 3 H, Ar-
H), 7.39 (d, J = 9.2 Hz, 2 H, Ar-H), 7.36–7.34 (m, 1 H, Ar-H), 7.13–7.09
(m, 1 H, Ar-H), 6.98 (d, J = 7.9 Hz, 2 H, Ar-H), 6.86 (d, J = 9.2 Hz, 2
H, Ar-H), 3.88 (s, 3 H, OCH3), 2.20 (s, 3 H, CH3) ppm. 13C NMR
(100 MHz, CDCl3): δ = 196.52, 163.43, 143.48, 138.28, 135.75, 133.05,
132.51, 132.23, 129.91, 129.45, 127.50, 127.18, 123.80, 123.59,
2969, 2844, 1622, 1505, 1442, 1377, 1344, 1260, 1208, 1165, 1103,
1027, 968, 920, 838, 754, 614 cm–1. HRMS (EI+): calcd. for C15H14O3
[M]+ 242.0943; found 242.0941.
(2-Hydroxy-5-nitrophenyl)(o-tolyl)methanone (3.31): White solid
(68 mg, 53 %), m.p. 96–98 °C. Rf (10 % ethyl acetate in hexane) =
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113.29, 55.54, 21.37 ppm. IR (neat): ν = 3251, 2934, 2841, 1629,
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0.54. H NMR (400 MHz, CDCl3): δ = 12.90 (s, 1 H, Ar-OH), 8.38 (dd,
1598, 1488, 1390, 1307, 1257, 1162, 1091, 1027, 942, 901762,
690 cm–1. HRMS (ES+): calcd. for C21H19NNaO4S [M + Na]+ 404.0932;
found 404.0930.
J = 9.2, 3.1 Hz, 1 H, Ar-H), 8.30 (d, J = 3.1 Hz, 1 H, Ar-H), 7.51–7.47
(m, 1 H, Ar-H), 7.39–7.29 (m, 3 H, Ar-H), 7.18 (d, J = 9.2 Hz, 1 H, Ar-
H), 2.35 (s, 3 H, CH3) ppm. 13C NMR (100 MHz, CDCl3): δ = 203.45,
167.98, 139.58, 136.16, 135.91, 131.57, 131.34, 131.26, 129.81,
N-(2-Benzoylphenyl)-4-methylbenzenesulfonamide (5.2):[11] Col-
ourless solid (148 mg, 84 %), m.p. 124–126 °C. Rf (20 % ethyl acetate
127.83, 125.74, 119.54, 118.76, 19.69 ppm. IR (KBr): ν = 3091, 3024,
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Eur. J. Org. Chem. 2017, 5080–5093
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© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim