10.1002/adsc.202001416
Advanced Synthesis & Catalysis
N-(4-Fluorophenyl)acetamide[25](2g)
Yield: 144 mg (94%); white powder; Rf
(EtOAc:Hexane, 3.0:7.0); mp: 139-141 °C; H NMR (400
MHz, CDCl3): δ 7.58 (br, 1H), 7.42-7.40 (d, J = 8.0 Hz,
2H), 6.98-6.96 (d, J = 8.0 Hz, 2H), 2.12 (s, 3H); 13C NMR
(100 MHz, CDCl3): δ 168.8, 160.8, 134.1, 122.1, 115.8,
24.5; IR (KBr): 3292, 2936, 1655, 1641, 762, 541cm-1;
HRMS (ESI): m/z [M+H]+ calculated for C8H9FNO
154.0663, found 154.0663.
Characterization data
N-Phenylacetamide[23] (2a)
=
0.35
1
Yield: 132 mg (97%); white solid; Rf
=
0.30
1
(EtOAc:Hexane, 3.0:7.0); mp: 112-115 °C; H NMR (600
MHz, CDCl3): δ 7.49-7.48 (d, J = 8.2 Hz, 2H), 7.32-7.30 (t,
J = 7.2 Hz, 2H), 7.12-7.09 (t, J = 7.2 Hz, 1H), 2.17 (s, 3H);
13C NMR (150 MHz, CDCl3): δ 168.8, 138.1, 129.1, 124.5,
120.2, 24.7; IR (KBr): 3294, 1664, 1598, 1435, 1322, 1264,
754, 510 cm-1; HRMS (ESI): m/z [M+H]+ calculated for
C8H10NO 136.0757, found 136.0759.
N-(4-Hydroxyphenyl)acetamide[27](2h)
N-Phenylisobutyramide[24] (2b)
Yield: 136 mg (90%); white crystalline solid; Rf = 0.25
1
(EtOAc:Hexane, 3.0:7.0); mp: 167-169 °C; H NMR (400
MHz, CDCl3 and 1 drop of CD3OD): δ 7.22-7.20 (d, J =
8.0 Hz, 2H), 6.69-6.67 (d, J = 8.0 Hz, 2H), 4.07 (broad,
OH), 2.02 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 169.8,
153.6, 130.1, 122.4, 122.3, 115.3, 23.3; IR (KBr): 3354,
2931, 1654, 1641, 1234, 863, 541 cm-1; HRMS (ESI): m/z
[M+H]+ calculated for C8H10NO2 152.0707, found
152.0707.
Yield: 150 mg (92%); white solid; Rf
=
0.50
1
(EtOAc:Hexane, 3.0:7.0); mp: 103-105 °C; H NMR (400
MHz, CDCl3): δ 8.05 (br, 1H), 7.56-7.54 (d, J = 7.2 Hz,
2H), 7.28-7.25 (t, J = 7.8 Hz, 2H), 7.10-7.06 (t, J = 7.2 Hz,
1H), 2.59-2.52 (m, 1H), 1.22-1.89 (d, J = 7.2 Hz, 6H); 13C
NMR (100 MHz, CDCl3): δ 176.1, 138.4, 128.9, 124.2,
120.3, 36.5, 19.7; IR (KBr): 3284, 3299, 2969, 1659, 1440,
1305, 1248, 754, 692, 514 cm-1; HRMS (ESI): m/z [M+H]+
calculated for C10H14NO 164.1070, found 164.1074.
N-(2-Hydroxyphenyl)acetamide[28](2i)
N-Phenylcyclopropanecarboxamide[24] (2c)
Yield: 133 mg (88%); white crystalline solid; Rf = 0.25
1
(EtOAc:Hexane, 3.0:7.0); mp: 207-209 °C; H NMR (400
MHz, CDCl3 and 1 drop of CD3OD): δ 7.16-7.14 (m, 1 H),
7.02-6.98 (m, 2H), 6.88-6.85 (m, 1 H), 2.01 (s, 3H); 13C
NMR (100 MHz, CDCl3): δ 169.5, 152.6, 130.6, 122.1,
114.2, 24.3; IR (KBr): 3352, 2938, 1645, 1232, 861, 547
cm-1; HRMS (ESI): m/z [M+H]+ calculated for C8H10NO2
152.0707, found 152.0704.
Yield: 145 mg (90%); white solid; Rf
=
0.50
1
(EtOAc:Hexane, 3.0:7.0); mp: 110-112 °C; H NMR (400
MHz, CDCl3): δ 8.41 (br, 1H), 7.51-7.49 (d, J = 8.0 Hz,
2H), 7.25-7.22 (t, J = 7.6 Hz, 2H), 7.06-7.02 (t, J = 7.2 Hz,
1H), 1.58-1.53 (m, 1H), 1.03-0.99 (m, 2H), 0.77-0.73 (m,
2H); 13C NMR (100 MHz, CDCl3): δ 172.9, 138.4, 128.9,
124.1, 120.2, 15.6, 7.9; IR (KBr): 3284, 3251, 2917, 1652,
1595, 1433, 1248, 951, 694, 502 cm-1; HRMS (ESI): m/z
[M+H]+ calculated for C10H11NO 162.0914, found
162.0919.
N-(4-Cyanophenyl)acetamide[29] (2j)
Yield: 114 mg (71%); white solid; Rf
=
0.50
1
(EtOAc:Hexane, 6.0:4.0); mp: 203-205 °C; H NMR (400
MHz, CDCl3): δ 7.67-7.65 (d, J = 8.4 Hz, 2H), 7.57-7.55
(d, J = 8.4 Hz, 2H), 2.16 (s, 3H); 13C NMR (100 MHz,
CDCl3): δ 169.6, 142.6, 133.4, 119.6, 119.2, 106.7, 24.5;
IR (KBr): 3304, 2924, 2855, 1732, 1669, 1215, 749, 669,
544 cm-1; LRMS (ESI): m/z [M+H]+ calculated for
C9H9N2O 161.0710, found 161.0610.
N-Phenylbenzamide[23](2d)
Yield: 185 mg (94%); white crystalline powder; Rf = 0.40
1
(EtOAc:Hexane, 2.5:7.5); mp: 160-163 °C; H NMR (600
N-(p-Tolyl)acetamide[23](2k)
MHz, CDCl3): δ 7.93 (br, 1H), 7.87-7.86 (d, J = 8.0 Hz,
2H), 7.65-7.64 (d, J = 8.0 Hz, 2H), 7.55-7.53 (t, J = 7.2 Hz,
1H), 7.48-7.46 (t, J = 8.0 Hz, 2H), 7.38-7.36 (t, J = 7.2 Hz,
2H), 7.16-7.14 (t, J = 7.2 Hz, 1H); 13C NMR (150 MHz,
CDCl3): δ 166.0, 138.1, 135.2, 132.0, 129.3, 128.9, 127.2,
124.8, 120.4 ; IR (KBr): 3344, 2920, 1655, 1599, 1438,
1322, 750, 649, 583 cm-1; HRMS (ESI): m/z [M+H]+
calculated for C13H12NO 198.0914, found 198.0916.
Yield: 129 mg (87%); colorless solid; Rf = 0.35
1
(EtOAc:Hexane, 3.0:7.0); mp: 151-153 °C; H NMR (600
MHz, CDCl3): δ 7.37-7.36 (d, J = 8.0 Hz, 2H), 7.11-7.09
(d, J = 8.0 Hz, 2H), 2.29 (s, 3H), 2.14 (s, 3H); 13C NMR
(100 MHz, CDCl3): δ 169.0, 135.5, 134.1, 129.6, 120.4,
24.5, 21.0; IR (KBr): 3290, 2965, 1662, 1543, 1378, 1211,
820, 510 cm-1; HRMS (ESI): m/z [M+H]+ calculated for
C9H12NO 150.0914, found 150.0913.
N-(4-Chlorophenyl)acetamide[25](2e)
N-(4-Ethylphenyl)acetamide[30](2l)
Yield: 160 mg (95%); white solid; Rf
=
0.35
1
(EtOAc:Hexane, 3.0:7.0); mp: 174-177 °C; H NMR (600
MHz, CDCl3): δ 7.46-7.45 (d, J = 8.0 Hz, 2H), 7.28-7.27 (t,
J = 8.0 Hz, 2H), 2.17 (s, 3H); 13C NMR (150 MHz,
CDCl3): δ 168.5, 139.5, 136.6, 129.5, 121.3, 29.9; IR
(KBr): 3297, 2922, 1662, 1601, 1489, 1261, 1091, 802,
507 cm-1; HRMS (ESI): m/z [M+H]+ calculated for
C8H9ClNO 170.0368, found 170.0368.
Yield: 145 mg (89%); white solid; Rf
=
0.35
1
(EtOAc:Hexane, 3.0:7.0); mp: 87-89 °C; H NMR (400
MHz, CDCl3): δ 7.38-7.36 (d, J = 8.5 Hz, 2H), 7.12-7.10
(d, J = 8.0 Hz, 2H), 2.61-2.55 (q, 2H), 2.13 (s, 3H), 1.20-
1.16 (t, J = 8.0 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ
169.0, 140.5, 135.8, 128.3, 120.5, 28.4, 24.5, 15.9; IR
(KBr): 3374, 2929, 1631, 1492, 1453, 1358, 1265, 1137,
1077, 948, 543 cm-1; HRMS (ESI): m/z [M+H]+calculated
for C10H14NO 164.1070, found 164.1075.
N-(4-Bromophenyl)acetamide[26](2f)
Yield: 199 mg (94%); white solid; Rf
=
0.35
1
N-(4-Methoxyphenyl)acetamide[23](2m)
(EtOAc:Hexane, 3.0:7.0); mp: 167-169 °C; H NMR (600
MHz, CDCl3): δ 7.45-7.41 (m, 4H), 2.16 (s, 3H); 13C NMR
(100 MHz, CDCl3): δ 168.7, 137.2, 132.1, 121.6, 117.0,
29.9; IR (KBr): 3486, 3295, 3269, 3181, 3132, 1671, 1512,
1488, 1312, 1257, 1170, 885, 655 cm-1; HRMS (ESI): m/z
[M+H]+ calculated for C8H9BrNO 213.9863, found
213.9864.
Yield: 143 mg (87%); white crystalline solid; Rf = 0.30
1
(EtOAc:Hexane, 3.0:7.0); mp: 126-129 °C; H NMR (400
MHz, CDCl3): δ 7.39-7.38 (d, J = 8.5 Hz, 2H), 6.86-6.84
(d, J = 8.5 Hz, 2H), 3.78 (s, 3H), 2.15 (s, 3H); 13C NMR
(150 MHz, CDCl3): δ 168.4, 156.7, 131.1, 122.2, 114.4,
55.7, 24.6; IR (KBr): 3302, 2923, 1655, 1564, 1134, 876,
6
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