´
E. Veverkova et al.
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General Procedure
A mixture of phenyl salicylate (or phenyl 4-methoxysalicylate) (0.1mol) and the amine (0.1mol) was
stirred under microwave irradiation in the microwave reactor (240W input power) for 5 min. After
cooling to room temperature, the reaction mixture was, treated with 50cm3 of CH2Cl2. The undis-
solved impurities were filtered off by suction, the solvent was evaporated, and formed phenol was
distilled off under reduced pressure. The residue was recrystallized from iso-hexane=ethyl acetate
(4=1) or purified by column chromatography on silica using CHCl3=ethyl acetate (19=1) as eluent
to give pure salicylanilides. The results are summarized in Table 1. Melting points and NMR data of
products 3a [5, 13], 3b [5, 14], 3c [15], 3d [2], 3e [2], 3h [16, 17], and 3j [16] were found to be
identical with the data described in literature.
2-Hydroxy-N-[4-[(1,3-dimethylbutyl)amino]phenyl]benzamide (3f, C19H24N2O2)
White solid; m.p. 56–58ꢁC; 1H NMR (CDCl3, 300 MHz): ꢀ ¼ 0.91 (d, J ¼ 6.0 Hz, CH3), 0.93
(d, J ¼ 6.0 Hz, CH3), 1.18 (d, J ¼ 6.0 Hz, CH3), 1.27–1.34 (m, CHAHB), 1.42–1.53 (m, CHAHB),
1.68–1.77 (m, CH(CH3)2), 3.48–3.55 (m, CHNH), 6.31 (d, J ¼ 9.0 Hz, 2Harom), 6.87 (t, J ¼ 8.1 Hz,
1Harom), 7.01 (d, J ¼ 9.0 Hz, 1Harom), 7.31 (d, J ¼ 9 Hz, 2Harom), 7.42 (t, J ¼ 8.1 Hz, 1Harom), 7.52 (d,
J ¼ 7.8 Hz, 2Harom), 7.86 (bs, NH), 12.18 (s, OH) ppm; 13C NMR (CDCl3, 75MHz): ꢀ ¼ 20.8, 22.5,
22.9, 25.1, 46.6, 113.7, 114.7, 118.8, 118.8, 123.7, 125.4, 134.3, 161.8, 168.3 ppm.
2-Hydroxy-N-(4-methyl-2-nitrophenyl)benzamide (3g, C14H12N2O4)
1
Yellow solid; m.p. 190ꢁC; H NMR (CDCl3, 300 MHz): ꢀ ¼ 2.43 (s, CH3), 6.96–7.06 (m, 2Harom),
7.46–7.56 (m, 3Harom), 8.10 (s, 1Harom), 8.73 (d, J ¼ 8.7 Hz, 1Harom), 11.39 (s, NH), 11.83 (s, OH)
ppm; 13C NMR (CDCl3, 75MHz): ꢀ ¼ 20.6, 114.5, 119.0, 119.5, 122.5, 125.8, 125.9, 131.8, 134.4,
135.3, 137.0, 162.3, 169.0 ppm.
2-Hydroxy-4-methoxy-N-(4-methyl-2-nitrophenyl)benzamide (3i, C15H14N2O5)
Yellow solid; m.p. 174–175ꢁC; 1H NMR (CDCl3, 300 MHz): ꢀ ¼ 2.42 (s, CH3), 3.85 (s, CH3),
6.50–6.56 (m, 2Harom), 7.51 (d, J ¼ 8.54Hz, 1Harom), 7.57 (d, J ¼ 8.85Hz, 1Harom), 8.07 (s, 1Harom),
8.70 (d, J ¼ 8.54Hz, 1Harom), 11.23 (s, NH), 12.17 (s, OH) ppm; 13C NMR (CDCl3, 75MHz):
ꢀ ¼ 20.6, 55.6, 101.8, 107.5, 108.0, 122.4, 125.8, 127.4, 132.2, 133.9, 136.6, 137.0, 164.7, 165.3,
168.8ppm.
N-(4-Aminophenyl)-2-hydroxy-4-methoxybenzamide (3k, C14H14N2O3)
Grey solid; m.p. 260–263ꢁC; 1H NMR (DMSO, 300 MHz): ꢀ ¼ 3.78 (s, OCH3), 6.52–6.54 (m, 2Harom),
7.39 (d, J ¼ 8.4 Hz, 2Harom), 7.80 (d, J ¼ 8.4 Hz, 2Harom), 8.06 (d, J ¼ 8.7 Hz, 1Harom), 10.46 (bs, NH),
12.39 (s, OH) ppm; 13C NMR (DMSO, 75MHz): ꢀ ¼ 55.5, 101.4, 106.3, 109.0, 122.2, 123.5, 127.7,
130.5, 137.7, 161.5, 163.84, 167.2ppm.
2-Hydroxy-4-methoxy-N-[4-(phenylamino)phenyl]benzamide (3l, C20H18N2O3)
1
Grey solid; m.p. 164–165ꢁC; H NMR (DMSO, 300MHz): ꢀ ¼ 3.79 (s, CH3), 6.48 (s, 1Harom), 6.50
(d, J ¼ 9.0 Hz, 1Harom), 6.71 (t, J ¼ 6.9 Hz, 1Harom), 7.03–7.09 (m, 4Harom), 7.19–7.24 (m, 2Harom),
7.51 (d, J ¼ 9.0 Hz, 2Harom), 7.98 (d, J ¼ 9.0 Hz, 1Harom), 8.13 (s, NH), 10.11 (s, NH), 12.65 (s, OH)
ppm; 13C NMR (DMSO, 75 MHz): ꢀ ¼ 55.2, 101.2, 110.6, 112.9, 118.1, 118.3, 121.2, 129.6, 132.8,
134.6, 138.3, 141.5, 161.9, 162.5, 166.4 ppm.