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Organic & Biomolecular Chemistry
Page 6 of 9
ARTICLE
Journal Name
(q, JC-F = 4 Hz), 124.2 (q, JC-F = 270 Hz), 123.9 (q, JC-F = 4 Hz), 123.8, NMR (400 MHz, DMSO-d6): δ = 12.03 (s, 1H), 8.68 (dd, J = 9.2,
120.5, 117.6 ppm; HRMS (ESI) calcd for C15H9F3NO3 [M - H]- 5.2 Hz, 1H), 7.95 – 7.93 (m, 2H), 7.75 (dDdO, JI: 1=0.910.43,9/3C.29OHBz0,0179H7)K,
308.0540, found 308.0559.
2-(2,4-Difluorobenzamido)benzoic acid (2j)
7.65 – 7.51 (m, 4H) ppm; 13C NMR (100 MHz, DMSO-d6) δ =
169.2, 165.0, 157.3 (d, JC-F = 240 Hz), 137.9 (d, JC-F = 3 Hz), 134.8,
Brown solid; 86% yield; mp = 167 C; FT-IR (neat): 3672, 3090, 132.6, 129.4 (2 × CH), 127.4 (2 × CH), 122.6 (d, JC-F = 7 Hz), 121.4
1743, 1681, 1450, 1165, 972, 840, 663 cm−1; 1H NMR (400 MHz, (d, JC-F = 22 Hz), 119.4 (d, JC-F = 5 Hz), 117.4 (d, JC-F = 23 Hz) ppm;
DMSO-d6): δ = 11.97 (s, 1H), 8.66 (d, J = 8.4 Hz, 1H), 8.04 – 7.96 HRMS (ESI) calcd for C14H9FNO3 [M - H]- 258.0572, found
(m, 2H), 7.64 (t, J = 7.9 Hz, 1H), 7.45 (t, J = 10.5 Hz, 1H), 7.28 – 258.0561.
7.19 (m, 2H) ppm; 13C NMR (100 MHz, DMSO-d6) δ = 169.8, 2-Benzamido-5-chlorobenzoic acid (2p)
164.7 (dd, JC-F = 251, 13 Hz), 161.2 (d, JC-F = 2 Hz), 160.4 (dd, JC-F Brown solid; 74% yield; mp = 248 C; FT-IR (neat): 3673, 3160,
= 251, 13 Hz), 140.8, 134.5, 133.3 (dd, JC-F = 11, 4 Hz), 131.6, 1745, 1680, 1450, 1178, 1195, 870, 667 cm−1; 1H NMR (400 MHz,
123.8, 120.9, 119.8 (dd, JC-F = 13, 4 Hz), 117.5, 113.0 (dd, JC-F
=
DMSO-d6): δ = 12.12 (s, 1H), 8.71 (d, J = 9.0 Hz, 1H), 7.97 (d, J =
22, 4 Hz), 105.4 (t, JC-F = 26 Hz) ppm; HRMS (ESI) calcd for 2.7 Hz, 1H), 7.94 (d, J = 7.0 Hz, 2H), 7.71 (dd, J = 9.0, 2.6 Hz, 1H),
C14H8F2NO3 [M - H]- 276.0478, found 276.0464.
2-(3-Nitrobenzamido)benzoic acid (2k)
7.66 – 7.62 (m, 1H), 7.58 (t, J = 7.6 Hz, 2H) ppm; 13C NMR (100
MHz, DMSO-d6) δ = 169.2, 165.1, 140.3, 134.6, 134.2, 132.7,
Yellow solid; 75% yield; mp = 191 C; FT-IR (neat): 3678, 3100, 130.8, 129.4 (2 × CH), 127.5 (2 × CH), 126.9, 122.2, 119.1 ppm;
1740, 1680, 1458, 1162, 978, 845, 663 cm−1; 1H NMR (400 MHz, HRMS (ESI) calcd for C14H9ClNO3 [M - H]- 274.0276, found
DMSO-d6): δ = 13.9 (br s, 1H), 12.42 (s, 1H), 8.74 (s, 1H), 8.62 (d, 274.0284.
J = 5.5 Hz, 1H), 8.48 (d, J = 7.3 Hz, 1H), 8.38 (d, J = 7.0 Hz, 1H), 2-Benzamido-5-bromobenzoic acid (2q)
8.06 (d, J = 7.1 Hz, 1H), 7.90 (t, J = 7.2 Hz, 1H), 7.68 (t, J = 7.0 Hz, Brown solid; 73% yield; mp = 173 C; FT-IR (neat): 3672, 3150,
1
1H), 7.25 (t, J = 7.0 Hz, 1H) ppm; 13C NMR (100 MHz, DMSO-d6) 1748, 1680, 1450, 1238, 890, 680 cm−1; H NMR (400 MHz,
δ = 170.5, 162.9, 148.5, 140.8, 136.3, 134.6, 133.8, 131.7, 131.2, DMSO-d6): δ = 11.67 (s, 1H), 8.60 (d, J = 8.4 Hz, 1H), 8.03 (dd, J
127.1, 124.0, 122.2, 120.8, 118.0 ppm; HRMS (ESI) calcd for = 8.0 Hz, 1H), 7.76 (d, J = 7.9 Hz, 1H), 7.68 – 7.65 (m, 2H), 7.54
C14H9N2O5 [M - H]- 285.0517, found 285.0504.
2-(Thiophene-2-carboxamido)benzoic acid (2l)
(t, J = 7.3 Hz, 1H), 7.47 (td, J = 7.8, 1.8 Hz, 1H), 7.24 (t, J = 7.6 Hz,
1H) ppm; 13C NMR (100 MHz, DMSO-d6) δ = 169.9, 165.9, 140.7,
Grey solid; 60% yield; mp = 198 C; FT-IR (neat): 3694, 2924, 138.8, 134.5, 133.8, 132.4, 131.7, 129.3, 128.5, 123.9, 120.5,
1
2854, 1755, 1697, 1450, 1311, 1018, 802, 648 cm−1; H NMR 119.2, 117.9 ppm; HRMS (ESI) calcd for C14H9BrNO3 [M - H]-
(400 MHz, DMSO-d6): δ = 13.85 (br s, 1H), 12.19 (s, 1H), 8.58 (d, 317.9771, found 317.9769.
J = 7.8 Hz, 1H), 8.05 (dd, J = 7.9, 1.5 Hz, 1H), 7.94 (dd, J = 5.0, 0.9 2-Benzamido-4-chlorobenzoic acid (2r)
Hz, 1H), 7.75 (dd, J = 3.7, 0.9 Hz, 1H), 7.67 – 7.63 (m, 1H), 7.28 Off yellow solid; 70% yield; mp = 223 C; FT-IR (neat): 3672,
(dd, J = 4.9, 3.8 Hz, 1H), 7.22 – 7.18 (m, 1H) ppm; 13C NMR (100 3050, 1743, 1658, 1404, 1026, 833, 694 cm−1; 1H NMR (400 MHz,
MHz, DMSO-d6) δ = 170.5, 159.9, 141.2, 140.1, 134.7, 133.0, DMSO-d6): δ = 14.08 (br s, 1H), 12.30 (s, 1H), 8.82 (d, J = 2.1 Hz,
131.7, 129.1, 128.9, 123.4, 120.3, 116.9 ppm; HRMS (ESI) calcd 1H), 8.06 (d, J = 8.6 Hz, 1H), 7.96 – 7.94 (m, 2H), 7.69 – 7.65 (m,
for C12H8NO3S [M - H]- 246.0230, found 246.0229.
2-(2-Naphthamido)benzoic acid (2m)
1H), 7.62 – 7.58 (m, 2H), 7.28 (dd, J = 8.6, 2.2 Hz, 1H) ppm; 13
NMR (100 MHz, DMSO-d6) δ = 169.8, 165.4, 142.6, 139.1, 134.5,
C
Brown solid; 66% yield; mp = 218 C; FT-IR (neat): 3690, 3150, 133.4, 132.9, 129.5 (2 × CH), 127.5 (2 × CH), 123.3, 119.6, 115.7
1750, 1680, 1443, 1178, 1099, 870, 668 cm−1; 1H NMR (400 MHz, ppm; HRMS (ESI) calcd for C14H9ClNO3 [M - H]- 274.0276, found
DMSO-d6): δ = 13.61 (br s, 1H), 11.83 (s, 1H), 8.73 (d, J = 8.3 Hz, 274.0267.
1H), 8.40 – 8.37 (m, 1H), 8.13 (d, J = 8.2 Hz, 1H), 8.07 – 8.03 (m, 2-Benzamido-4,5-dimethylbenzoic acid (2s)
2H), 7.91 (d, J = 7.1 Hz, 1H), 7.71 (t, J = 7.8 Hz, 1H), 7.69 – 7.61 Brown solid; 52% yield; mp = 200 C; FT-IR (neat): 3670, 3150,
1
(m, 3H), 7.25 (t, J = 7.6 Hz, 1H) ppm; 13C NMR (100 MHz, DMSO- 1748, 1650, 1424, 1028, 850, 690 cm−1; H NMR (400 MHz,
d6) δ = 170.0, 167.3, 141.2, 134.6, 134.5, 133.8, 131.6, 131.5, DMSO-d6): δ = 12.11 (s, 1H), 8.54 (s, 1H), 7.93 (d, J = 7.4 Hz, 2H),
130.0, 128.9, 127.7, 127.0, 125.9, 125.6, 125.5, 123.7, 120.7, 7.80 (s, 1H), 7.65 – 7.56 (m, 3H), 2.29 (s, 3H), 2.22 (s, 3H) ppm;
117.8 ppm; HRMS (ESI) calcd for C18H12NO3 [M - H]- 290.0823, 13C NMR (100 MHz, DMSO-d6) δ = 170.5, 164.8, 143.9, 139.5,
found 290.0850.
2-Acetamidobenzoic acid (2n)
135.0, 132.5, 132.1, 131.4, 129.4, 127.3, 121.2, 114.4, 20.6, 19.2
ppm; HRMS (ESI) calcd for C16H14NO3 [M - H]- 268.0979, found
Dark brown solid; 61% yield; mp = 169 C (lit.,53 167-170 C); FT- 268.0978.
IR (neat): 3649, 3255, 2924, 1760, 1681, 1512, 1257, 694 cm−1; N-(Pyridin-2-yl)benzamide (5a)
1H NMR (400 MHz, DMSO-d6): δ = 13.6 (br s, 1H), 11.08 (s, 1H), White solid; 95% yield; mp = 84 C (Lit.46 mp 82-84); H NMR
8.46 (d, J = 8.3 Hz, 1H), 7.96 (dd, J = 7.9, 1.4 Hz, 1H), 7.59 – 7.55 (400 MHz, CDCl3): δ = 9.22 (s, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.11
(m, 1H), 7.13 (t, J = 7.2 Hz, 1H), 2.13 (s, 3H) ppm; 13C NMR (100 (d, J = 4.0 Hz, 1H), 7.93 – 7.90 (m, 2H), 7.75 – 7.70 (m, 1H), 7.55
MHz, DMSO-d6) δ = 169.9, 168.9, 141.3, 134.4, 131.5, 123.0, – 7.51 (m, 1H), 7.47 – 7.43 (m, 2H), 7.0 (dd, J = 7.1, 5.0 Hz, 1H)
120.3, 116.9, 25.4 ppm; HRMS (ESI) calcd for C9H8NO3 [M - H]- ppm; 13C NMR (100 MHz, CDCl3) δ = 166.0, 151.7, 147.8, 138.5,
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178.0510, found 178.0511.
134.4, 132.2, 128.7 (2 × CH), 127.3 (2 × CH), 119.8, 114.3 ppm.
2-Benzamido-5-fluorobenzoic acid (2o)
Experimental procedure for the preparation of 4a.
Reddish brown solid; 78% yield; mp = 228 C; FT-IR (neat): 3741, To a stirred solution of 2-benzamidobenzoic acid (2a) (0.41
1
3132, 3008, 1795, 1668, 1419, 1381, 1180, 933, 694 cm−1; H mmol) in acetonitrile (5 mL) at 0 °C (ice bath) were added POCl3
6 | J. Name., 2012, 00, 1-3
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