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Catalysis Science & Technology
Page 7 of 11
Journal Name
DOI: 10.1039/C7CY00761B
ARTICLE
168.3, 134.7, 131.1, 128.3, 127.0, 40.8; GCꢀMS (EI): m/z 135 m/z 226 [M+]; Rνmax (cmꢀ1): 3443, 3418, 3344, 2956, 2906,
[M+]; Rνmax (cmꢀ1): 3326, 3086, 3054, 2960, 1639, 1553, 1492, 2822, 1633, 1537, 1505, 1110.
1409, 1310, 1164, 697, 642.
-(4-Chlorophenethyl)benzamide 3j
Known compound (3418ꢀ95ꢀ9);Yellow solid; M.p. 147–149 135oC; 1H NMR (600 MHz, CDCl3) δ 7.71 (d,
oC;1H NMR (600 MHz, CDCl3) δ 7.69 (d,
= 7.2 Hz, 2H), 7.40–7.38 (m, 2H), 7.14 (d, = 7.8 Hz, 2H), 6.67 (d,
7.50–7.48 (t, = 7.2 Hz, 1H), 7.43–7.40 (t, = 7.2 Hz, 2H), Hz, 2H), 6.23 (s, 1H), 4.51 (d,
= 5.4 Hz, 2H), 3.69 (s, 2H);13C
7.29 (m, 2H), 7.17 (d, = 7.8 Hz, 2H), 6.15 (s, 1H), 3.69 (d, NMR (150 MHz, CDCl3) δ 166.1, 146.1, 137.7, 132.9, 129.4,
6.6 Hz, 2H), 2.92–2.90 (t,
= 6.6 Hz, 2H);13C NMR (150 MHz, 128.8, 128.4, 127.6, 115.3, 44.0; GCꢀMS (EI): m/z 260 [M+];
CDCl3) δ 167.6, 137.4, 134.4, 132.4, 131.5, 130.2, 128.8,
νmax (cmꢀ1): 3474, 3304, 3084, 2926, 1638, 1554, 1517, 1093,
N
-(4-Aminobenzyl)-4-chlorobenzamide 3p
Known compound (895774ꢀ33ꢀ1); Yellow solid; M.p. 133–
= 8.4 Hz, 2H),
= 8.4
N
J
J
J
J
J
J
J
J
J =
J
R
128.6, 126.8, 41.1, 35.0; GCꢀMS (EI): m/z 259 [M+]; Rνmax 849, 806, 669.
(cmꢀ1): 3350, 2971, 2930, 2863,1640, 1537, 1488, 1311, 1293,
1191, 1091, 1014, 859, 837, 724, 714, 694, 538.
N
-(4-Aminobenzyl)-6-chloronicotinamide 3q
Yellow solid; M.p. 122–124oC;1H NMR (600 MHz, CDCl3) δ
8.71 (d, = 2.4 Hz, 1H), 8.08–8.06 (m, 1H), 7.39 (d, = 8.4
Known compound (254889ꢀ06ꢀ0);White solid; M.p. 110– Hz, 1H), 7.12 (d, = 8.4 Hz, 2H), 6.65 (d, = 8.4 Hz, 2H), 6.51
113oC;1H NMR (600 MHz, CDCl3) δ 7.79 (d, = 5.4 Hz, 2H), 3.76 (s, 2H); 13C NMR (150
= 7.8 Hz, 2H), (s, 1H), 4.50 (d,
7.51–7.47 (m, 2H), 7.44–7.42 (t, = 7.2 Hz, 2H), 7.39 (d, MHz, CDCl3) δ163.2, 153.2, 147.0, 145.2, 137.0, 128.4, 128,
4.8 Hz, 1H), 7.25 (s, 2H), 6.63 (s, 1H), 4.74 (d,
= 5.4 Hz, 2H); 126.1, 123.3, 114.3, 43.0; GCꢀMS (EI): m/z 261 [M+]; Rνmax
N
-(2-Chlorobenzyl)benzamide 3k
J
J
J
J
J
J
J
J =
J
13C NMR (150 MHz, CDCl3) δ 167.4, 135.6, 134.3, 133.8, (cmꢀ1): 3418, 2924, 2855, 1641, 1588, 1573, 1503, 1461, 1106.
131.7, 130.6, 129.6, 129.1, 128.7, 127.2, 127.0, 42.1; GCꢀMS HRMS (ESI): m/z calcd for C13H13ClN3O+ [M+H]+: 262.0742,
(EI): m/z 245 [M+]; Rνmax (cmꢀ1): 3287, 3063, 2926, 2850, found: 262.0745.
1632, 1545, 1489, 1469, 1308, 1263, 751, 696.
)- -(1-Phenylethyl)benzamide 3l
Known compound (4108ꢀ58ꢀ1);Yellow solid; M.p. 122– 125–127oC; H NMR (500 MHz, CDCl3) δ 7.74 (d,
123oC;1H NMR (600 MHz, CDCl3) δ 7.77 (d,
= 7.8 Hz, 2H), 2H), 7.48 (d, = 9.0 Hz, 2H), 6.44 (s, 1H), 3.43–3.39 (m, 2H),
7.49 (t, = 7.2 Hz, 1H), 7.44 – 7.40 (m, 4H), 7.37 (t, = 7.2 1.58 (t, = 7.3 Hz, 2H), 1.41–1.36 (m, 2H), 0.94 (t, = 7.3 Hz,
Hz, 2H), 7.29 (t, = 7.2 Hz, 1H), 6.32 (d,
= 4.2Hz, 1H), 5.37– 3H); 13C NMR (125 MHz, CDCl3) δ 166.8, 137.7, 134.2, 128.5,
5.33 (m, 1H), 1.62 (d,
N
-butyl-4-iodobenzamide 3r
(
S N
Known compound (250739ꢀ37ꢀ8); Light yellow solid; M.p.
1
J
= 7.5Hz,
J
J
J
J
J
J
J
J
J
= 6.6 Hz, 3H); 13C NMR (150 MHz, 98.1, 39.9, 31.6, 20.2, 13.8; GCꢀMS (EI): m/z 303 [M+]; Rνmax
CDCl3) δ 166.6, 143.1, 134.7, 131.5, 128.8, 128.6, 127.5, (cmꢀ1): 3304, 2967, 2931, 2871, 1622, 1541, 1479, 1384, 1303,
126.9, 126.3, 49.2, 21.7; GCꢀMS (EI): m/z 225 [M+]; Rνmax 1009, 840, 677.
(cmꢀ1): 3304, 3062, 3031, 2966, 2922, 2864, 1635, 1535, 1120, N-butyl-4-cyanobenzamide 3s
702.
-Phenylbenzamide 3m
Known compound (409108ꢀ81ꢀ2); Light yellow solid; M.p. 71–
N
73 oC; 1H NMR (500 MHz, CDCl3) δ 7.88–7.95 (m, 2H), 7.69–
o
Known compound (93ꢀ98ꢀ1); Yellow solid; M.p. 162–164 C; 7.67 (m, 2H), 6.77ꢀ6.75 (m, 1H), 3.43ꢀ3.39 (m, 2H), 1.59ꢀ1.56
= 7.8 Hz, 3H), 7.64 (d, (m, 2H),1.39ꢀ1.35 (m, 2H), 0.92 (t,
1H NMR (600 MHz, CDCl3) δ 7.87 (d, = 7.5 Hz, 3H); 13C NMR
= 7.8 Hz, 2H), 7.56–7.54 (t, = 7.2 Hz, 1H), 7.49–7.47 (t, (125 MHz, CDCl3) δ 165.7, 138.7, 132.2, 127.6, 117.9, 114.6,
7.2 Hz, 2H), 7.38–7.36 (t, = 7.8 Hz, 2H), 7.17–7.14 (t, J ν
= 7.2 40.0, 31.4, 20.0, 13.6; GCꢀMS (EI): m/z 202 [M+]; R max (cmꢀ1):
J
J
J
J
J =
J
Hz, 1H); 13C NMR (150 MHz, CDCl3) δ 165.8, 137.9, 135.0, 3302, 3082, 2956, 2930, 2871, 2232, 1636, 1552, 1497, 1317,
131.9, 129.2, 128.8, 127.1, 124.6, 120.2; GCꢀMS (EI): m/z 197 1116, 859, 684.
[M+]; Rνmax (cmꢀ1): 3343, 3052, 1655, 1600, 1578, 1534, 1438, 4-amino-
1322, 1260, 750, 716, 690, 648, 509.
N
-butylbenzamide 3t
Known compound (51207ꢀ84ꢀ2); oil; H NMR (500 MHz,
actone) δ 7.94 (s, 1H), 7.57 (d, = 8.5 Hz, 2H), 6.54 (d, = 9.0
Known compound (133053ꢀ84ꢀ6);Yellow solid; M.p. 210– Hz, 2H), 5.56 (s, 2H), 3.21ꢀ3.17 (m, 2H), 1.48ꢀ1.45 (m, 2H),
213oC;1H NMR (600 MHz, CDCl3) δ 8.11 (d, = 7.3 Hz, 3H); 13C NMR (125
= 7.8Hz, 1H), 1.32ꢀ1.27 (m, 2H), 0.88 (t,
7.91–7.90 (t, = 1.2 Hz, 2H), 7.82 (s, 1H), 7.69 (d, = 8.4 Hz, MHz,
6ꢀactone) δ 166.1, 151.4, 128.6, 121.5, 112.5, 38.6, 31.5,
1H), 7.62–7.60 (m, 1H), 7.54–7.52 (t,
= 7.8 Hz, 2H), 7.40– 19.7, 13.7; GCꢀMS (EI): m/z 192 [M+]; Rνmax (cmꢀ1): 3440,
7.38 (t,
= 7.8 Hz, 1H), 2.45 (s, 3H); 13C NMR (150 MHz, 3357, 3082, 2926, 1637, 1550, 1539, 1301, 842, 673.
1
d
6ꢀ
N
-(2-Methyl-3-nitrophenyl)benzamide 3n
J
J
J
J
J
J
d
J
J
CDCl3) δ 165.8, 151.1, 137.4, 134.0, 132.5, 129.0, 128.2, N-butyl-4-vinylbenzamide 3u
127.1, 127.0, 124.9, 121.2, 13.8; GCꢀMS (EI): m/z 256 [M+]; Known compound (29568ꢀ16ꢀ9); Light yellow solid; M.p. 62–
R
N
ν
max (cmꢀ1): 3344, 3031, 2969, 1655, 1583, 1324.
64 oC; 1H NMR (500 MHz, CDCl3) δ 7.71–7.74 (m, 2H), 7.41–
7.42 (m, 2H), 6.69ꢀ6.75 (m, 1H), 6.50 (s, 1H), 5.79–5.82 (m,
-(4-Aminobenzyl)benzamide 3o
Known compound (32478ꢀ65ꢀ2); Dark solid; M.p. 142– 1H), 5.32–5.34 (m, 1H), 3.40–3.45 (m, 2H), 1.56–1.60 (m, 2H),
143oC;1H NMR (600 MHz, CDCl3) δ 7.77–7.76 (m, 2H), 7.50– 1.35–1.43 (m, 2H), 0.94 (t, = 7.5 Hz, 3H); 13C NMR (125
7.47 (m, 1H), 7.43–7.40 (m, 2H), 7.15 (d, = 8.4 Hz, 2H), MHz, CDCl3) δ 167.3, 140.4, 136.0, 133.9, 127.2, 126.2, 115.7,
6.68–6.66 (m, 2H), 6.28 (s, 1H), 4.52 (d,
= 5.4 Hz, 2H), 3.68 39.8, 31.7, 20.2, 13.8; GCꢀMS (EI): m/z 203 [M+]; R max (cmꢀ1):
J
J
J
ν
(s, 2H); 13C NMR (150 MHz, CDCl3) δ 167.2, 146.0, 134.6, 3314, 3086, 2961, 2930, 2861, 1634, 1544, 1504, 1314, 1116,
131.5, 129.4, 128.6, 127.9, 126.9, 115.3, 43.9; GCꢀMS (EI): 993, 908, 857, 677.
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