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3326, 3464 cm–1; H NMR (600 MHz, DMSO-d6) δ 5.59 (s, 2H), 3H), 7.25–7.35 (m, 3H), 7.64–7.69 (m, 1H), 7.69–7.72 (m, 1H), 7.91
6.53 (d, J = 8.6 Hz, 2H), 6.86 (bs, 1H), 7.53 (bs, 1H), 7.60 (d, J = (bs, 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 20.9, 124.6, 128.1
8.6 Hz, 2H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 112.5, 121.0, (2C), 131.7, 134.3, 137.4, 168.0; elemenDtaOlI: a1n0.a1l0y3s9is/C4cRaAlc1d568f2oJr
129.2, 151.7, 168.2; elemental analysis calcd for [C7H8N2O]: C, [C8H9NO]: C, 71.09; H, 6.71; N, 10.36, found: C, 71.04; H, 6.78; N,
61.75; H, 5.92; N, 20.58, found: C, 61.79; H, 5.87; N, 20.30.
9.98.
p-Hydroxybenzamide (2c).20 White powder, purified by column o-Methylbenzamide (2i).8g Colorless needles, purified by column
chromatography on silica gel (tetrahydrofran/diethyl ether 4:6–10:0, chromatography on silica gel (ethyl acetate/n-hexane 2:3); mp
gradient); mp 157.1–159.2 °C (lit.20 148 °C); IR (KBr) 1247, 1403, 140.1–140.5 °C (lit.8g 140 °C); IR (KBr) 1140, 1395, 1623, 1656,
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1558, 1618, 1649, 3124, 3340, 3417 cm–1; 1H NMR (600 MHz, 3187, 3368 cm–1; H NMR (600 MHz, DMSO-d6) δ 2.36 (s, 3H),
DMSO-d6) δ 6.78 (d, J = 8.6 Hz, 2H), 7.08 (bs, 1H), 7.68–7.79 (m, 7.18–7.24 (m, 2H), 7.28–7.37 (m, 3H), 7.68 (bs, 1H); 13C{1H} NMR
3H), 9.94 (s, 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 114.7, (150 MHz, DMSO-d6) δ 19.6, 125.4, 127.0, 129.1, 130.4, 135.1,
125.0, 129.5, 160.2, 167.7; elemental analysis calcd for [C7H7NO2]: 137.1, 171.0; elemental analysis calcd for [C8H9NO]: C, 71.09; H,
C, 61.31; H, 5.15; N, 10.21, found: C, 61.13; H, 5.14; N, 10.01.
6.71; N, 10.36, found: C, 71.35; H, 6.72; N, 10.36.
m-Hydroxybenzamide (2d).21 White powder, purified by column m-Chlorobenzamide (2j).8g Colorless plates, purified by sequential
chromatography on silica gel (2-propanol/n-hexane/ethyl acetate column chromatography on silica gel (n-hexane/ethyl acetate 1:1;
1:20:200); mp 165.1–168.0 °C (lit.21 167–168 °C); IR (KBr) 1256, ethyl acetate only; tetrahydrofuran only) and activated carbon
1450, 1580, 1653, 3247, 3400 cm–1; 1H NMR (600 MHz, DMSO-d6) treatment; mp 132.6–133.4 °C (lit.8g 134–136 °C); IR (KBr) 1123,
δ 6.88–6.92 (m, 1H), 7.20–7.24 (m, 1H), 7.24–7.30 (m, 3H), 7.86 (s, 1389, 1432, 1569, 1626, 1658, 3181, 3366 cm–1; 1H NMR (600 MHz,
1H), 9.60 (s, 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 114.5, DMSO-d6) δ 7.46–7.52 (m, 1H), 7.54 (bs, 1H), 7.56–7.61 (m, 1H),
118.0, 118.1, 129.2, 135.8, 157.3, 168.0; elemental analysis calcd for 7.81–7.86 (m, 1H), 7.89–7.94 (m, 1H), 8.10 (bs, 1H); 13C{1H} NMR
[C7H7NO2]: C, 61.31; H, 5.15; N, 10.21, found: C, 61.23; H, 5.12; N, (150 MHz, DMSO-d6) δ 126.2, 127.3, 130.3, 131.1, 133.1, 136.3,
10.05.
166.4; elemental analysis calcd for [C7H6NClO]: C, 54.04; H, 3.89;
N, 9.00, found: C, 53.96; H, 3.89; N, 8.95.
o-Hydroxybenzamide (2e).7 Colorless plates, purified by column
chromatography on silica gel (chloroform only); mp 138.2– p-Formylbenzamide (2k).22 White powder, purified by column
139.2 °C; IR (KBr) 1253, 1359, 1424, 1447, 1493, 1590, 1630, 1675, chromatography on silica gel (n-hexane/ethyl acetate 1:3); mp
3189, 3395 cm–1; H NMR (600 MHz, DMSO-d6) δ 6.83–6.89 (m, 155.4–159.2 °C; IR (KBr) 1212, 1397, 1607, 1670, 1698, 3194,
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2H), 7.37–7.42 (m, 1H), 7.84 (dd, J = 1.6, 8.0 Hz, 1H), 7.89 (bs, 1H), 3288, 3354 cm–1; 1H NMR (600 MHz, DMSO-d6) δ 7.60 (bs,
8.39 (bs, 1H), 13.0 (s, 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 1H), 7.96–8.00 (m, 2H), 8.03–8.08 (m, 2H), 8.17 (bs, 1H), 10.08 (s,
114.4, 117.4, 118.3, 128.1, 134.1, 161.1, 172.1; elemental analysis 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 128.1, 129.3, 137.8,
calcd for [C7H7NO2]: C, 61.31; H, 5.15; N, 10.21, found: C, 61.22; 139.3, 167.0, 192.9; elemental analysis calcd for [C8H7NO2]: C,
H, 5.21; N, 10.01.
64.42; H, 4.73; N, 9.39, found: C, 64.69; H, 4.85; N, 9.16.
p-Methoxybenzamide (2f).6 Colorless plates, purified by column p-Nitrobenzamide (2l).6 Colorless needles, purified by column
chromatography on silica gel (tetrahydrofuran/diethyl ether 0:10– chromatography on silica gel (triethylamine/2-propanol/chloroform
10:0, gradient); mp 164.3–169.3 °C; IR (KBr) 1146, 1253, 1396, 0.05:3:7); mp 197.1–200.0 °C; IR (KBr) 1346, 1413, 1526, 1600,
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1422, 1573, 1643, 3170, 3391 cm–1; 1H NMR (600 MHz, CD3OD) δ 1678, 3177, 3477 cm–1; H NMR (600 MHz, CD3OD) δ 8.05–8.08
3.82 (s, 3H), 6.93–6.97 (m, 2H), 7.81–7.85 (m, 2H); 13C{1H} NMR (m, 2H), 8.29–8.33 (m, 2H); 13C{1H} NMR (150 MHz, CD3OD) δ
(150 MHz, CD3OD) δ 55.9, 114.7, 126.9, 130.6, 164.1, 172.0; 124.6, 130.0, 140.9, 151.2, 170.1; elemental analysis calcd for
elemental analysis calcd for [C8H9NO2]: C, 63.56; H, 6.00; N, 9.27, [C7H6N2O3]: C, 50.61; H, 3.64; N, 16.86, found: C, 50.67; H, 3.69;
found: C, 63.37; H, 6.00; N, 9.23.
N, 16.64.
p-Methylbenzamide (2g).8g Colorless plates, purified by column 2,3,4,5,6-Pentafluorobenzamide (2m).7 Colorless plates, purified
chromatography on silica gel (acetone/dichloromethane 2:5); mp by column chromatography on silica gel (ethyl acetate/n-hexane
157.6–159.0 °C (lit.8g 159–160 °C); IR (KBr) 1397, 1414, 1571, 1:2); mp 146.8–147.2 °C; IR (KBr) 1001, 1493, 1675, 3186, 3358
1618, 1671, 3168, 3343 cm–1; 1H NMR (600 MHz, DMSO-d6) δ cm–1; 1H NMR (600 MHz, DMSO-d6) δ 8.16 (bs, 1H), 8.30 (bs, 1H);
2.34 (s, 3H), 7.22–7.30 (m, 3H), 7.75–7.80 (m, 2H), 7.89 (bs, 1H); 13C{1H} NMR (150 MHz, DMSO-d6) δ 112.9 (t, J = 21.6 Hz),
13C{1H} NMR (150 MHz, DMSO-d6) δ 20.9, 127.5, 128.7, 131.5, 135.9–137.9 (m), 139.9–141.9 (m), 141.8–143.9 (m), 158.3;
141.0, 167.8; elemental analysis calcd for [C8H9NO]: C, 71.09; H, 13C{19F} NMR (150 MHz, DMSO-d6); δ 112.9 (d, J = 8.7 Hz), 136.9,
140.9, 142.9, 158.3; 19F NMR (564 MHz, DMSO-d6) δ –162.0––
6.71; N, 10.36, found: C, 70.99; H, 6.66; N, 10.26.
161.3 (m, 2F), –154.0––153.4 (m, 1F), –142.3––141.9 (m, 2F);
elemental analysis calcd for [C7H2F5NO]: C, 39.83; H, 0.96; N, 6.64,
m-Methylbenzamide (2h).8g Colorless plates, purified by column
chromatography on silica gel (n-hexane/ethyl acetate 2:3); mp 91.0–
found: C, 40.00; H, 6.65; N, 1.09.
92.4 °C (lit.8g 92–93 °C); IR (KBr) 687, 1114, 1387, 1432, 1616,
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1650, 3195, 3376 cm–1; H NMR (600 MHz, DMSO-d6) δ 2.34 (s,
6 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 2012