The Journal of Organic Chemistry
Page 4 of 6
δ 7.53 (d, J = 7.3 Hz, 2H), 7.35 – 7.31 (m, 1H), 7.28 – 7.18 (m,
N-phenylpentanamide (9a) 4d Purification by chromatography
5H), 7.08 (d, J = 7.4 Hz, 2H), 2.35 (s, 3H); 13C{1H} NMR (100
MHz, CDCl3) δ 173.6, 173.0, 139.3, 135.0, 132.2, 129.5, 129.4,
128.7, 128.4, 128.2, 25.8.
(petroleum ether/ EtOAc = 5:1) afforded 9a as a white solid (12.9
mg, 73%); mp 59-60 °C; 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J
= 7.9 Hz, 1H), 7.30 (t, J = 7.7 Hz, 1H), 7.09 (t, J = 7.3 Hz, 1H),
2.35 (t, J = 7.6 Hz, 1H), 1.77 – 1.65 (m, 1H), 1.46 – 1.32 (m, 1H),
0.93 (t, J = 7.3 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ
171.8, 138.2, 129.0, 124.3, 120.1, 37.6, 27.8, 22.5, 13.9.
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5
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4-Methyl-N-(p-tolyl)benzamide (7b)19 Purification by chroma-
tography (petroleum ether/ EtOAc = 6:1) afforded 7b as a white
solid (20.6 mg, 96%); mp 210-211 °C; 1H NMR (400 MHz,
CDCl3) δ 7.80 (s, 1H), 7.67 (d, J = 7.4 Hz, 2H), 7.44 (d, J = 7.6
Hz, 2H), 7.17 (d, J = 7.5 Hz, 2H), 7.07 (d, J = 7.5 Hz, 2H), 2.33 (s,
3H), 2.25 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ 165.8,
142.3, 135.6, 134.2, 132.3, 129.6, 129.5, 127.1, 120.4, 21.6, 21.0.
3-Methyl-N-(m-tolyl)benzamide (7c)20 Purification by chroma-
tography (petroleum ether/ EtOAc = 6:1) afforded 7c as a white
solid (21.6 mg, 96%); mp 125-126 °C; 1H NMR (400 MHz,
CDCl3) δ 7.91 (brs, 1H), 7.66 – 7.63 (m, 2H), 7.50 (s, 1H), 7.43 –
7.41 (m, 1H), 7.33 (s, 1H), 7.25 – 7.21 (m, 1H), 6.96 – 6.94 (m,
1H), 2.40 (s, 3H), 2.35 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3)
δ 166.1, 139.1, 138.7, 138.1, 135.2, 132.6, 129.0, 128.7, 127.9,
125.4, 124.1, 121.0, 117.4, 21.6, 21.5.
N-(p-tolyl)pentanamide (9b)19 Purification by chromatography
(petroleum ether/ EtOAc = 6:1) afforded 9b as a white solid (11.5
1
mg, 60%); mp 67-68 °C; H NMR (400 MHz, CDCl3) δ 7.40 –
9
7.38 (m, 2H), 7.19 (brs, 1H), 7.12 – 7.10 (m, 2H), 2.36 – 2.30 (m,
5H), 1.72 – 1.68 (m, 2H), 1.41 – 1.38 (m, 2H), 0.94 (t, J = 7.3 Hz,
3H); 13C{1H} NMR (100 MHz, CDCl3) δ 171.5, 135.5, 133.9,
129.6, 120.0, 37.7, 27.9, 22.5, 21.0, 14.0.
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19
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25
26
27
28
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31
32
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35
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N-(4-methoxyphenyl)pentanamide (9c)32 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 9c as a
1
white solid (16.6 mg, 80%); mp 79-80 °C; H NMR (400 MHz,
CDCl3) δ 7.47 (s, 1H), 7.41 (d, J = 8.9 Hz, 2H), 6.82 (d, J = 8.9
Hz, 2H), 3.77 (s, 3H), 2.31 (t, J = 7.6 Hz, 2H), 1.68 – 1.66 (m,
2H), 1.38 – 1.35 (m, 2H), 0.92 (t, J = 7.3 Hz, 3H); 13C{1H} NMR
(100 MHz, CDCl3) δ 171.6, 156.3, 131.2, 121.9, 114.0, 55.6, 37.4,
27.9, 22.5, 14.0.
2-Methyl-N-(o-tolyl)benzamide (7d) 21 Purification by chroma-
tography (petroleum ether/ EtOAc = 6:1) afforded 7d as a white
solid (16 mg, 71%); mp 141-142 °C; 1H NMR (400 MHz, CDCl3)
δ 7.92 – 7.90 (m, 1H), 7.45 – 7.44 (m, 1H), 7.32 – 7.28 (m, 1H),
7.22 – 7.15 (m, 5H), 7.05 (t, J = 7.2 Hz, 1H), 2.46 (s, 3H), 2.23 (s,
3H); 13C{1H} NMR (100 MHz, CDCl3) δ 168.2, 136.7, 135.9,
131.5, 130.7 (2C), 130.4, 129.2, 127.0, 126.8, 126.1, 125.5, 123.2,
20.1, 18.1.
N-(4-fluorophenyl)pentanamide (9d)17b Purification by chro-
matography (petroleum ether/ EtOAc = 6:1) afforded 9d as a
1
white solid (10.3 mg, 53%); mp 50-51 °C; H NMR (400 MHz,
CDCl3) δ 7.47 – 7.44 (m, 2H), 7.00 – 6.96 (m, 2H), 2.33 (t, J =
7.5 Hz, 1H), 1.77 – 1.63 (m, 1H), 1.41– 1.36 (m, 2H), 0.93 (t, J =
7.2 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3) δ 171.7, δ 159.5
(d, J = 243.4 Hz), 134.1, 121.9 (d, J = 7.6 Hz), 115.7 (d, J = 21.9
Hz), 37.5, 27.8, 22.5, 13.9.
3-Methoxy-N-(3-methoxyphenyl)benzamide (7e)22 Purification
by chromatography (petroleum ether/ EtOAc = 4:1) afforded 7e as
1
a white solid (23.1 mg, 90%); mp 96-97 °C; H NMR (400 MHz,
CDCl3) δ 7.92-7.89 (m, 1H), 7.43 – 7.42 (m, 2H), 7.37 – 7.35 (m,
2H), 7.26 – 7.22 (m, 1H), 7.10 – 7.06 (m, 2H), 6.70 (dd, J = 8.2,
2.2 Hz, 1H), 3.85-3.84 (m, 3H), 3.82-3.81 (m, 3H); 13C{1H} NMR
(100 MHz, CDCl3) δ 165.7, 160.4, 160.2, 139.3, 136.6, 129.9
(2C), 118.8, 118.2, 112.6, 112.4, 110.7, 106.0, 55.6, 55.5.
4-Methoxy-N-(4-methoxyphenyl)benzamide (7f)23 Purification
by chromatography (petroleum ether/ EtOAc = 2:1) afforded 7f as
a white solid (18.2 mg, 71%); mp 206-207 °C; 1H NMR (400
MHz, DMSO-d6) δ 9.97 (s, 1H), 7.94 (d, J = 8.5 Hz, 2H), 7.65 (d,
J = 8.7 Hz, 2H), 7.05 (d, J = 8.5 Hz, 2H), 6.91 (d, J = 8.7 Hz, 2H),
3.83 (s, 3H), 3.74 (s, 3H); 13C{1H} NMR (100 MHz, DMSO-d6) δ
164.5, 161.8, 155.4, 132.4, 129.5, 127.1, 122.0, 113.7, 113.6, 55.4,
55.2.
N-([1,1'-biphenyl]-4-yl)pentanamide (9e)30 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 9e as a
white solid (14.2 mg, 56%); mp 169-170 °C; 1H NMR (400 MHz,
CDCl3) δ 7.61 – 7.53 (m, 6H), 7.42 (t, J = 7.6 Hz, 2H), 7.32 (t, J =
7.3 Hz, 2H), 2.38 (t, J = 7.6 Hz, 2H), 1.77 – 1.70 (m, 2H), 1.47 –
1.38 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H); 13C{1H} NMR (100 MHz,
CDCl3) δ 171.7, 140.7, 137.5, 137.2, 128.9, 127.7, 127.0, 120.3,
37.7, 27.9, 22.5, 13.9.
N-(naphthalen-2-yl)pentanamide (9f)31 Purification by chro-
matography (petroleum ether/ EtOAc = 6:1) afforded 9f as a white
solid (18.2 mg, 80%); mp 84-85 °C; 1H NMR (400 MHz, CDCl3)
δ 8.21 (s, 1H), 7.79 – 7.77 (m, 3H), 7.47 – 7.38 (m, 3H), 7.30 (brs,
1H), 2.42 (t, J = 7.5 Hz, 2H), 1.78 – 1.74 (m, 2H), 1.47 – 1.44 (m,
2H), 0.97 (t, J = 7.3 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3) δ
171.5, 135.4, 133.9, 130.6, 128.7, 127.6, 127.5, 126.5, 124.9,
119.8, 116.5, 37.6, 27.7, 22.4, 13.8.
4-Fluoro-N-(4-fluorophenyl)benzamide (7g)19 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 7g as a
white solid (21.9 mg, 94%); mp 180-181 °C; 1H NMR (400 MHz,
DMSO-d6) δ 10.32 (s, 1H), 8.05 – 8.01 (m, 2H), 7.79 – 7.76 (m,
2H), 7.39 – 7.34 (m, 2H), 7.21 – 7.17 (m, 2H); 13C{1H} NMR
(100 MHz, DMSO-d6) δ 165.3, 163.6 (d, J = 151.1 Hz), 158.4 (d,
J = 240.4 Hz), 135.4, 131.2 (d, J = 3.0 Hz), 130.4 (d, J = 9.1 Hz),
122.3 (d, J = 7.8 Hz), 115.3 (dd, J = 22.0, 15.3 Hz, 2C).
3-Methyl-N-phenylbutanamide (9g)26 Purification by chroma-
tography (petroleum ether/ EtOAc = 6:1) afforded 9g as a white
solid (15.8 mg, 89%); mp 112-113 °C; 1H NMR (400 MHz,
CDCl3) δ 7.52 – 7.50 (m, 2H), 7.33 – 7.29 (m, 2H), 7.21 (brs, 1H),
7.10 (t, J = 7.3 Hz, 1H), 2.22 (s, 3H), 1.02 (d, J = 5.8 Hz, 6H);
13C{1H} NMR (100 MHz, CDCl3) δ 170.9, 138.1, 129.1, 124.4,
120.0, 47.3, 26.4, 22.6.
4-Chloro-N-(4-chlorophenyl)benzamide (7h)19 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 7h as a
white solid (23.1 mg, 87%); mp 202-203 °C; 1H NMR (400 MHz,
DMSO-d6) δ 10.44 (s, 1H), 7.98 (d, J = 8.4 Hz, 2H), 7.81 (d, J =
8.7 Hz, 2H), 7.62 (d, J = 8.4 Hz, 2H), 7.42 (d, J = 8.7 Hz, 2H);
13C{1H} NMR (100 MHz, DMSO-d6) δ 164.5, 138.0, 136.6, 133.4,
129.7, 128.6, 128.5, 127.5, 121.9.
N-phenylcyclopropanecarboxamide (9h)22 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 9h as a
white solid (13.8 mg, 86%); mp 111-112 °C; 1H NMR (400 MHz,
CDCl3) δ 7.87 (s, 1H), 7.51 (d, J = 7.8 Hz, 2H), 7.30 – 7.26 (m,
2H), 7.07 (t, J = 7.2 Hz, 1H), 1.25 (s, 1H), 1.06 – 1.05 (m, 2H),
0.82 – 0.80 (m, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ 172.3,
138.3, 129.0, 124.1, 119.9, 15.8, 8.1.
4-Bromo-N-(4-bromophenyl)benzamide (7i)23 Purification by
chromatography (petroleum ether/ EtOAc = 6:1) afforded 7i as a
white solid (30.6 mg, 87%); mp 223-224 °C; 1H NMR (400 MHz,
CDCl3) δ 10.44 (s, 1H), 7.90 (d, J = 8.5 Hz, 2H), 7.75 – 7.74 (m,
4H), 7.53 (d, J = 8.7 Hz, 2H); 13C{1H} NMR (100 MHz, CDCl3) δ
164.7, 138.4, 133.7, 131.5 (2C), 129.8, 125.5, 122.3, 115.6.
2-Methyl-N-phenylbutanamide (9i)25 Purification by chroma-
tography (petroleum ether/ EtOAc = 6:1) afforded 9i as a white
solid (3.8 mg, 22%); mp 95-96 °C; 1H NMR (400 MHz, CDCl3) δ
7.54– 7.52 (m, 2H), 7.33 – 7.29 (m, 2H), 7.17 (brs, 1H), 7.09 (t, J
= 7.3 Hz, 1H), 2.29 – 2.22 (m, 1H), 1.83 – 1.72 (m, 1H), 1.56 –
1.47 (m, 1H), 1.23 (d, J = 6.8 Hz, 3H), 0.97 (t, J = 7.4 Hz, 3H);
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