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G. Sheng et al.
Paper
Synthesis
N-(4-Acetylphenyl)benzamide (3l)
13C NMR (126 MHz, CD3OD): δ = 167.29, 166.72, 164.72, 133.54,
White solid; yield: 172 mg (72%); mp 180–181 °C (EtOAc) [Lit.33 205
132.02, 131.22, 127.00, 115.04, 114.86.
HRMS (ESI): m/z [M – H]+ calcd for C14H9O3NF: 258.0567; found:
°C (CHCl3)].
1H NMR (400 MHz, CDCl3, TMS): δ = 8.4 (m, 2 H), 8.1 (d, J = 8.4 Hz, 2
H), 8.0 (s, 1 H), 7.9 (d, J = 8.4 Hz, 2 H), 7.50–7.53 (m, 3 H), 2.66 (s, 3 H).
258.0561.
4-Methyl-N-(2-pyridyl)benzamide (3r)
White solid, yield: 32 mg (15%); mp 120–121 °C [Lit.38 123.6–124.3
13C NMR (100 MHz, CDCl3): δ = 196.82, 151.88, 137.97, 135.41,
131.56, 130.31, 129.49, 129.34, 128.83, 122.09, 26.92.
°C].
HRMS (ESI): m/z [M + H]+ calcd for C15H14O2N: 240.1019; found:
1H NMR (500 MHz, CDCl3): δ = 8.11 (d, J = 4.1 Hz, 1 H), 7.40 (dd, J =
15.5, 1.7 Hz, 1 H), 7.32 (dd, J = 8.3, 5.5 Hz, 2 H), 7.02 (t, J = 8.6 Hz, 2 H),
6.60 (dd, J = 6.9, 5.2 Hz, 1 H), 6.36 (d, J = 8.4 Hz, 1 H).
13C NMR (126 MHz, CDCl3): δ = 163.01, 161.06, 158.43, 148.23,
137.45, 134.9, 128.94, 115.50, 115.33, 113.32, 106.88.
240.1017.
N-(4-Acetylphenyl)-2-hydroxybenzamide (3m)
Yellow solid; yield: 171 mg (67%); mp 167–168 °C (EtOAc) [Lit.34 205–
207 °C].
1H NMR (400 MHz, CDCl3, TMS): δ = 12.46 (s, 1 H), 8.07–8.15 (m, 3 H),
7.92 (d, J = 8 Hz, 2 H), 7.49 (dd, J1 = 15.6 Hz, J2 = 1.6 Hz, 1 H), 7.23 (dd,
J1 = 8 Hz, J2 = 1.6 Hz, 1 H), 7.05 (d, J = 8 Hz, 1 H), 6.93 (dd, J1 = 15.2 Hz,
J2 = 8 Hz, 1 H), 2.68 (s, 3 H,).
HRMS (ESI): m/z [M + H]+ calcd for C12H10ON2F: 217.0772; found:
217.0770.
N-(2-Furyl)benzamide (3s)
Grayish-white solid; yield: 140 mg (75%); mp 119–120 °C [Lit.39 121–
13C NMR (100 MHz, CDCl3): δ = 196.58, 160.29, 148.90, 141.93,
122 °C].
138.31, 135.33, 133.20, 129.60, 122.13, 120.63, 119.51, 116.65, 26.92.
1H NMR (500 MHz, CDCl3): δ = 8.15 (s, 1 H), 8.01 (d, J = 3.4 Hz, 1 H),
7.79 (d, J = 6.7 Hz, 2 H), 7.58 (s, 1 H), 7.47 (q, J = 6.5 Hz, 3 H), 6.64 (d,
J = 1.7 Hz, 1 H).
HRMS (ESI): m/z [M + H]+ calcd for C15H14O3N: 256.0968; found:
256.0967.
N-(4-Acetylphenyl)-4-chlorobenzamide (3n)
13C NMR (100 MHz, CDCl3): δ = 162.77, 147.52, 144.63, 129.95,
129.18, 124.27, 121.04, 116.48, 112.71.
Yellow solid; yield: 199 mg (73%); mp 164–165 °C (EtOAc).
HRMS (ESI): m/z [M + H]+ calcd for C11H10O2N: 188.0706; found:
188.0703.
1H NMR (400 MHz, CDCl3, TMS): δ = 8.39 (d, J = 8 Hz, 2 H), 8.09 (d, J =
8 Hz, 2 H), 7.99 (s, 1 H), 7.89 (d, J = 8 Hz, 2 H), 7.47 (d, J = 8 Hz, 2 H),
2.67 (s, 3 H).
N-(2-Furyl)-4-methylbenzamide (3t)
13C NMR (100 MHz, CDCl3): δ = 196.74, 151.66, 138.08, 136.98,
Grayish-white solid; yield: 181 mg (90%); mp 132.0–132.9 °C (EtOAc)
[Lit.40 108 °C (EtOH)].
1H NMR (500 MHz, CDCl3): δ = 8.12 (s, 1 H), 7.98 (d, J = 3.4 Hz, 1 H),
7.68 (d, J = 8.3 Hz, 2 H), 7.57 (d, J = 1.5 Hz, 1 H), 7.27 (d, J = 7.3 Hz, 2 H),
6.65–6.62 (m, 1 H), 2.41 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 147.62, 145.04, 144.43, 140.20,
129.66, 123.77, 120.77, 116.20, 112.65, 21.12.
134.16, 130.44, 129.50, 129.10, 128.79, 122.00, 26.92.
HRMS (ESI): m/z [M + H]+ calcd for C15H13O2NCl: 274.0629; found:
274.0630.
3-Phenyl-N-(4-tolyl)acryamide (3o)
Yellow solid; yield: 126 mg (53%); mp 154–157 °C [Lit.35 156–157 °C].
1H NMR (400 MHz, CDCl3, TMS): δ = 7.8 (d, J = 12 Hz, 1 H), 7.7 (s, 1 H),
7.6 (d, J = 8 Hz, 2 H), 7.58 (d, J = 8 Hz, 2 H), 7.3–7.4 (m, 3 H), 7.25 (d, J =
7.6 Hz, 2 H), 7.14 (d, J = 16 Hz, 1 H), 2.4 (s, 3 H).
HRMS (ESI): m/z [M + H]+ calcd for C12H12O2N: 202.0863; found:
202.0859.
13C NMR (100 MHz, CDCl3): δ = 145.12, 140.35, 139.75, 136.15,
135.99, 129.66, 129.49, 128.96, 127.53, 121.22, 119.18, 21.25.
4-Acetyl-N-(2-furyl)benzamide (3u)
Yellow flake solid; yield: 185 mg (81%); mp 151.2–151.7 °C (EtOAc).
HRMS (ESI): m/z [M + H]+ calcd for C16H16ON: 238.1226; found:
238.1221.
1H NMR (500 MHz, CDCl3): δ = 8.24 (s, 1 H), 8.09 (s, 1 H), 8.08–8.05
(m, 2 H), 7.92 (d, J = 8.6 Hz, 2 H), 7.62 (d, J = 1.5 Hz, 1 H), 6.67 (dd, J =
3.4, 1.0 Hz, 1 H), 2.65 (s, 3 H).
13C NMR (100 MHz, CDCl3): δ = 196.56, 147.36, 145.26, 137.94,
129.41, 124.79, 121.19, 117.46, 112.93, 26.75.
4-[(4-Fluorobenzoyl)amino]benzoic Acid (3p)
Brown solid; yield: 109 mg (42%); mp >300 °C [Lit.36 300 °C].
1H NMR (500 MHz, CD3OD): δ = 8.57 (d, J = 3.2 Hz, 2 H), 8.45 (s, 1 H),
8.14 (d, J = 8.8 Hz, 2 H), 7.89 (d, J = 8.7 Hz, 2 H), 7.27 (s, 2 H).
13C NMR (126 MHz, CD3OD): δ = 165.26, 163.25, 149.91, 136.65,
HRMS (ESI): m/z [M + H]+ calcd for C13H12O3N: 230.0812; found:
230.0812.
132.42, 130.13, 126.93, 124.66, 121.70, 121.12, 115.28.
HRMS (ESI): m/z [M + H]+ calcd for C14H11O3NF: 260.0717; found:
260.0715.
Acknowledgement
We are grateful for the financial support from the Natural Science
Foundation of Shandong Province (ZR2012CL15) and High-level Per-
sonnel Scientific Funds of Qingdao Agricultural University (630427).
2-[(4-Fluorobenzoyl)amino]benzoic Acid (3q)
Brown solid; yield: 101 mg (39%); mp >300 °C (EtOAc) [Lit.37 183 °C].
1H NMR (500 MHz, CD3OD): δ = 8.07 (s, 1 H,), 8.06 (s, 1 H), 8.05 (d, J =
2.1 Hz, 2 H), 7.20 (d, J = 1.9 Hz, 1 H), 7.18 (s, 3 H), 7.17 (d, J = 1.8 Hz, 1
H).
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2015, 47, 949–954