Molecules 2019, 24, 3838
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-Ethylbenzamide (2e): Known compound. 132.6 mg, 89% yield. White solid. m.p.: 160.2–162.5 C.
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H-NMR (CDCl , 400 MHz)
δ 7.74 (d, J = 8.3 Hz, 2H), 7.27 (d, J = 8.3 Hz, 2H), 6.06 (bs, 2H), 2.70
q, J = 7.6 Hz, 2H), 1.25 (t, J = 7.6 Hz, 3H); C-NMR (CDCl , 100 MHz) δ 169.7, 148.8, 130.9, 128.2, 127.6,
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3
(
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8.9, 15.4.
-(Chloromethyl)benzamide (2f): Known compound. 107.2 mg, 63% yield. White solid. m.p.:
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33.3–135.1 C. H-NMR (d -DMSO, 400 MHz)
δ
7.92 (bs, 1H), 7.84 (d, J = 8.2 Hz, 2H), 7.38 (d, J = 8.0 Hz,
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2
H), 7.30 (bs, 1H), 4.56 (s, 2H); C-NMR (d -DMSO, 100 MHz) δ 167.8, 145.9, 132.6, 127.3, 125.9, 62.5.
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-Fluorobenzamide (2g): Known compound. 127.0 mg, 91% yield. White solid. m.p.: 155.3–155.5 C.
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H-NMR (d -DMSO, 400 MHz)
δ
8.03 (bs, 1H), 8.00–7.96 (m, 2H), 7.43 (bs, 1H), 7.34–7.28 (m, 2H);
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C-NMR (d -DMSO, 100 MHz)
δ 166.8, 163.9 (d, J = 245.8 Hz), 130.7 (d, J = 11.5 Hz), 130.1 (d, J = 9.0 Hz),
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15.1 (d, J = 21.6 Hz); F NMR (d -DMSO, 376 MHz) δ −109.6.
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-Chlorobenzamide (2h): Known compound. 130.1 mg, 84% yield. White solid. m.p.: 177.4–178.8 C.
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13
H-NMR (CDCl , 400 MHz)
δ
7.77–7.74 (m, 2H), 7.45–7.42 (m, 2H), 5.85 (bs, 2H); C-NMR (CDCl3,
00 MHz) δ 168.3, 138.5, 131.8, 129.1, 128.9.
-Bromobenzamide (2i): Known compound. 165.0 mg, 83% yield. White solid. m.p.: 188.9–191.6 C.
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1
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1
H-NMR (d -DMSO, 400 MHz)
δ 8.08 (bs, 1H), 7.87–7.84 (m, 2H), 7.72–7.68 (m, 2H), 7.49 (bs, 1H);
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13
C-NMR (d -DMSO, 100 MHz) δ 166.9, 133.4, 131.2, 129.6, 125.0.
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-Formylbenzamide (2j): Known compound. 91.0 mg, 61% yield. White solid. m.p.: 178.9–182.1 C.
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1
H-NMR (d -DMSO, 400 MHz)
δ
10.09 (bs, 1H), 8.19 (bs, 1H), 8.07 (d, J = 7.9 Hz, 2H), 7.99 (d, J = 8.0 Hz,
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13
2
H), 7.62 (bs, 1H); C-NMR (d -DMSO, 100 MHz) δ 192.9, 167.0, 139.3, 137.8, 129.3, 128.1.
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-Acetylbenzamide (2k): Known compound. 110.8 mg, 68% yield. Yellow solid. m.p.: 192.5–194.1 C.
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13
H-NMR (d -DMSO, 400 MHz)
δ 8.15 (bs, 1H), 8.04–7.98 (m, 4H), 7.57 (bs, 1H), 2.62 (s, 3H); C-NMR
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(
d -DMSO, 100 MHz) δ 197.7, 167.1, 138.6, 138.1, 128.1, 127.7, 26.9.
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0
[
1,1 -Biphenyl]-4-carboxamide (2l): Known compound. 164.1 mg, 83% yield. White solid. m.p.:
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2
7
32.1–234.5 C. H-NMR (d -DMSO, 400 MHz)
δ
8.08 (bs, 1H), 8.02 (d, J = 8.4 Hz, 2H), 7.80 (bs, 1H),
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.78–7.75 (m, 3H), 7.53 (t, J = 7.3 Hz, 2H), 7.44 (t, J = 7.2 Hz, 2H); C-NMR (d -DMSO, 100 MHz)
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δ 167.5, 142.7, 139.2, 133.1, 129.0, 128.1, 128.0, 126.8, 126.4.
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-Naphthamide (2m): Known compound. 94.6 mg, 55% yield. White solid. m.p.: 204.8–206.2 C.
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13
H-NMR (d -DMSO, 400 MHz)
δ
8.36 (d, J = 7.3 Hz, 1H), 8.05–8.00 (m, 3H), 7.70–7.55 (m, 5H); C-NMR
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(
d -DMSO, 100 MHz) δ 170.5, 134.6, 133.2, 129.7 × 2, 128.1, 126.6, 126.1, 125.6, 125.1, 124.9.
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Anthracene-9-carboxamide (2n): Known compound. 90.7 mg, 41% yield. Yellow solid. m.p.:
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86.2–188.6 C. H-NMR (d -DMSO, 400 MHz) δ 8.68 (bs, 1H), 8.30 (bs, 1H), 8.16 (d, J = 7.9 Hz, 2H),
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1
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8
13
.08 (d, J = 8.8 Hz, 3H), 7.64–7.57 (m, 4H); C-NMR (d -DMSO, 100 MHz)
δ
170.2, 133.7, 130.7, 128.3,
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26.8 × 2, 126.2, 125.5, 125.4.
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-Aminobenzamide (2o): Known compound. 130.5 mg, 96% yield. Yellow solid. m.p.: 110.1–111.5 C.
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H-NMR (CDCl , 400 MHz)
δ
7.36 (dd, J = 7.9 and 1.3 Hz, 1H), 7.25–7.20 (m, 1H), 6.68 (d, J = 8.2 Hz, 1H),
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.66–6.62 (m, 1H), 5.90 (bs, 2H), 5.67 (bs, 2H); 13C-NMR (CDCl , 100 MHz)
δ
171.8, 149.6, 133.1, 128.1,
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17.6, 116.5, 114.1.
-Amino-6-methylbenzamide (2p): Known compound. 139.9 mg, 93% yield. White solid. m.p.:
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43.7–144.8 C. H-NMR (d -DMSO, 400 MHz) δ 7.63 (bs, 1H), 7.42 (bs, 1H), 6.92 (t, J = 7.7 Hz, 1H), 6.51
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(
d, J = 7.9 Hz, 1H), 6.39 (d, J = 7.2 Hz, 1H), 4.90 (bs, 2H), 2.21 (s, 3H); C-NMR (d -DMSO, 100 MHz)
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δ 170.5, 145.4, 134.2, 128.7, 123.0, 117.9, 112.7, 19.9.
-Amino-5-methylbenzamide (2q): Known compound. 135.9 mg, 90% yield. Yellow solid. m.p.:
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72.6–174.3 C. H-NMR (d -DMSO, 400 MHz) δ 7.65 (bs, 1H), 7.34 (bs, 1H), 6.95 (dd, J = 8.2 and 1.5 Hz,
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H), 6.59 (d, J = 8.2 Hz, 1H), 6.31 (bs, 2H), 2.15 (s, 3H); C-NMR (d -DMSO, 100 MHz) δ 171.3, 147.8,
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32.7, 128.6, 122.7, 116.5, 113.7, 20.0.
-Amino-4-methylbenzamide (2r): Known compound. 146.1 mg, 97% yield. White solid. m.p.:
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48.9–149.5 C. H-NMR (d -DMSO, 400 MHz) δ 7.62 (bs, 1H), 7.43 (d, J = 8.1 Hz, 1H), 6.92 (bs, 1H),
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.53 (bs, 2H), 6.47 (s, 1H), 6.29 (d, J = 8.5 Hz, 1H), 2.16 (s, 3H); C-NMR (d -DMSO, 100 MHz) δ 171.2,
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50.3, 141.6, 128.8, 116.4, 115.6, 111.1, 21.0.