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Electronic Supplementary Information (ESI)
Sulphuric acid immobilized on silica gel (H2SO4-SiO2) as an eco-friendly catalyst for transamidation Sk. Rasheed,a,b D. Nageswar Rao, a,b A. Siva Reddy, a,b Ravi Shankar,b and Parthasarathi Das a,b,*
aAcademy of Scientific and Innovative Research (AcSIR); bMedicinal Chemistry Division, Indian Institute of Integrative Medicine(CSIR) Canal Road, Jammu-180001, J & K, India; E-mail: [email protected]
Table of contents
The1H and 13C NMR spectra of compounds Page 1-42
N-(p-Tolyl)benzamide(1a): H1 NMR & C13 NMR
Electronic Supplementary Material (ESI) for RSC Advances.This journal is © The Royal Society of Chemistry 2015
2
0102030405060708090100110120130140150160170f1 (ppm)
20.9
5
120.
29
127.
0212
8.78
129.
6113
1.77
134.
2713
5.08
135.
36
165.
70
Methyl 4-(3-methoxybenzamido)benzoate(1b): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
2.99
2.91
2.08
1.09
1.00
1.99
1.98
3.87
3.88
7.15
7.16
7.17
7.18
7.20
7.21
7.23
7.23
7.37
7.39
7.41
7.43
7.45
7.63
7.66
7.66
7.71
7.74
7.76
3
0102030405060708090100110120130140150160f1 (ppm)
55.4
655
.56
114.
3311
4.88
120.
4312
1.10
122.
6612
2.92
129.
5412
9.89
130.
02
159.
5815
9.85
162.
26
2,6-Dimethyl-N-phenylbenzamide(1c): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
6.12
3.12
3.16
0.94
0.96
1.18
1.00
2.28
3.88
7.09
7.10
7.12
7.13
7.14
7.15
7.38
7.40
7.45
7.49
7.49
4
0102030405060708090100110120130140150160170f1 (ppm)
18.4
9
55.5
0
112.
66
117.
9911
8.99
127.
4612
8.28
129.
7613
3.86
135.
6013
5.93
159.
95
165.
88
3-Methoxy-N-(pyrimidin-2-yl)benzamide(1d): H1 NMR & C13 NMR
5
N-(Cyclopropylmethyl)-3-methoxybenzamide(1e): H1 NMR & C13 NMR
6
0102030405060708090100110120130140150160170f1 (ppm)
3.51
10.7
2
44.9
9
55.4
6
112.
35
117.
5411
8.62
129.
54
136.
27
159.
81
167.
32
(3-Methoxyphenyl)(morpholino)methanone(1f): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.89
3.99
2.92
2.78
1.00
3.45
3.64
3.76
3.77
3.82
6.94
6.96
7.28
7.30
7.32
7.34
7.34
7
N-(Naphthalen-2-yl)-1-naphthamide(1g): H1 NMR & C13 NMR
8
0102030405060708090100110120130140150160170f1 (ppm)
116.
78
119.
7812
4.76
125.
1412
5.21
125.
2612
6.66
127.
4512
7.61
127.
7812
8.47
128.
9513
0.08
130.
8013
1.17
133.
7713
3.86
135.
42
167.
69
N-(Cyclopropylmethyl)-1-naphthamide(1h): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
2.10
2.06
1.12
2.05
0.98
1.12
2.09
1.06
2.11
1.00
0.29
0.30
0.31
0.33
0.55
0.56
0.58
0.60
1.07
1.08
1.09
1.09
1.11
1.12
1.13
1.14
3.39
3.41
3.43
6.12
7.44
7.46
7.48
7.50
7.52
7.52
7.54
7.54
7.56
7.56
7.57
7.61
7.62
7.86
7.86
7.90
7.92
8.30
8.32
9
0102030405060708090100110120130140150160170180f1 (ppm)
3.53
10.8
4
44.8
7
124.
7612
4.88
125.
4312
6.40
127.
0712
8.31
130.
1213
0.46
133.
6613
4.77
169.
54
Naphthalen-1-yl(piperidin-1-yl)methanone(1i): H1 NMR & C13 NMR
10
N-(Pyridin-2-yl)-1-naphthamide(1j): H1 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
1.02
1.10
2.12
2.06
1.02
1.05
1.06
0.98
1.02
1.00
6.85
6.86
6.88
7.40
7.48
7.66
7.69
7.70
7.81
7.88
7.90
8.31
8.33
8.40
8.41
9.35
11
N-(4-Bromopyridin-2-yl)-1-naphthamide(1k): H1 NMR & C13 NMR
12
N-(2-Chloropyridin-3-yl)-1-naphthamide(1l): H1 NMR & C13 NMR
13
N-(Pyrimidin-2-yl)-1-naphthamide(1m): H1 NMR & C13 NMR
-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.010.5f1 (ppm)
1.12
3.01
1.00
2.09
1.02
1.00
0.99
7.40
7.40
7.41
7.42
7.45
7.47
7.48
7.49
7.50
7.50
7.51
7.52
7.53
7.55
7.59
7.61
7.80
7.81
7.81
7.82
7.84
7.84
7.86
7.87
7.89
8.03
8.05
8.28
8.30
8.98
9.00
14
N-Phenylpivalamide(2a): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
9.01
1.00
2.02
1.98
1.32
7.08
7.10
7.12
7.30
7.32
7.34
7.52
7.54
7.07.17.27.37.47.57.67.77.8f1 (ppm)
1.00
2.02
1.98
7.08
7.10
7.12
7.30
7.32
7.34
7.52
7.54
0102030405060708090100110120130140150160170180190f1 (ppm)
27.6
6
39.6
2
119.
9612
4.22
128.
98
138.
01
176.
61
15
N-(p-Tolyl)pivalamide(2b): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
9.07
3.04
2.17
2.03
1.31
2.31
7.11
7.13
7.40
7.41
7.17.27.37.47.57.6f1 (ppm)
2.17
2.03
7.11
7.13
7.40
7.41
0102030405060708090100110120130140150160170180f1 (ppm)
20.8
3
27.6
6
39.5
2
120.
05
129.
4313
3.79
135.
47
176.
45
16
Methoxyphenyl)pivalamide(2c): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)
9.08
2.94
1.91
1.00
1.93
1.30
3.79
6.84
6.86
7.27
7.41
7.43
0102030405060708090100110120130140150160170180f1 (ppm)
27.6
7
39.4
2
55.5
0
114.
05
121.
95
131.
12
156.
33
176.
53
17
N-(2,6-Dimethylphenyl)pivalamide(2d): H1 NMR & C13 NMR
0102030405060708090100110120130140150160170180f1 (ppm)
18.2
9
27.8
1
39.2
8
127.
1012
8.14
133.
9913
5.45
176.
56
18
Methyl 2-methoxy-4-pivalamidobenzoate(2e): H1 NMR & C13 NMR
19
N-(2-Iodophenyl)pivalamide(2f): H1 NMR & C13 NMR
0102030405060708090100110120130140150160170180190f1 (ppm)
27.7
2
40.1
8
90.1
0
121.
7012
5.71
129.
29
138.
2813
8.69
176.
82
20
N-(Pyridin-2-yl)pivalamide(2g): H1 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
9.05
1.04
1.07
1.00
2.07
1.33
7.02
7.03
7.04
7.05
7.68
7.70
7.72
7.72
8.04
8.24
8.26
7.07.58.0f1 (ppm)
1.04
1.07
1.00
2.07
7.02
7.03
7.04
7.05
7.68
7.70
7.72
7.72
8.04
8.24
8.26
N-(5-
Bromopyridin-2-yl)pivalamide(2h): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
8.99
1.04
0.92
0.99
1.00
1.31
7.79
7.81
8.17
8.18
8.20
8.29
21
N-(2-Chloropyridin-3-yl)pivalamide(2i): H1 NMR
22
N-(Thiazol-2-yl)pivalamide(2j): H1 NMR & C13 NMR
0102030405060708090100110120130140150160170180190f1 (ppm)
27.2
1
39.1
4
113.
72
137.
27
159.
08
176.
43
23
N-Phenylformamide(3a): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
3.09
0.96
4.06
2.06
0.98
1.03
1.04
1.00
7.09
7.11
7.16
7.18
7.19
7.29
7.31
7.32
7.34
7.36
7.54
7.56
8.18
8.33
8.67
8.70
8.96
0102030405060708090100110120130140150160f1 (ppm)
118.
8112
0.26
124.
8112
5.30
129.
0812
9.75
136.
8813
7.12
159.
99
163.
34
24
Methyl 4-formamidobenzoate(3b): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
6.07
1.98
2.03
4.08
1.00
1.04
3.91
7.15
7.17
7.64
7.66
8.00
8.03
8.05
8.44
8.85
25
Methyl 4-formamido-2-methoxybenzoate(3c): H1 NMR & C13 NMR
26
N-(2-Hydroxy-5-methylphenyl)formamide(3d): H1 NMR & C13 NMR
27
N-(2-Iodophenyl)formamide(3e): H1 NMR & C13 NMR
28
N-(Pyridin-3-yl)formamide(3f): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
1.00
1.00
0.96
2.38
1.15
7.36
7.48
7.50
8.24
8.26
8.47
8.71
29
N-(2-Chloropyridin-3-yl)formamide(3g): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
1.06
1.02
0.98
1.00
1.10
7.29
7.29
7.31
7.77
8.10
8.15
8.56
8.76
8.78
30
N-(5-Bromopyridin-2-yl)formamide(3h): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
1.00
0.90
1.11
1.12
2.01
1.09
1.05
0.98
0.83
6.81
6.83
7.77
7.77
7.79
7.79
7.83
7.83
7.85
7.85
8.17
8.19
8.36
8.51
8.87
9.28
9.31
9.47
0102030405060708090100110120130140150160170f1 (ppm)
111.
9111
5.19
116.
17
141.
1914
1.22
148.
5914
9.30
149.
5114
9.54
159.
25
162.
83
31
N-(Thiazol-2-yl)formamide(3i): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
1.11
1.05
1.00
7.05
7.06
7.47
7.48
8.63
32
N-Phenethylformamide(3j): H1 NMR & C13 NMR
0102030405060708090100110120130140150160170f1 (ppm)
35.4
737
.65
39.2
943
.31
126.
6112
6.87
128.
6712
8.78
128.
8212
8.91
137.
7213
8.62
161.
60
164.
83
33
Methyl 2-formamido-3-(1H-indol-3-yl)propanoate(3k): H1 NMR & C13 NMR
34
Piperidine-1-carbaldehyde(3l): H1 NMR
Morpholine-4-carbaldehyde(3m): H1 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
2.06
2.00
2.09
2.13
1.00
3.39
3.40
3.42
3.57
3.58
3.59
3.65
3.67
3.68
3.69
3.70
3.71
8.06
35
N- (p-Tolyl)acetamide(3n): H1 NMR
N-(4-Methoxyphenyl)acetamide(3o): H1 NMR
N-(4-
36
Fluorophenyl)acetamide(3p): H1 NMR & C13 NMR
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.74
2.47
2.31
1.00
2.16
6.97
6.99
7.02
7.43
7.44
7.45
7.45
7.46
7.50
37
N-(4-(Trifluoromethoxy)phenyl)acetamide(3q): H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)
3.12
1.91
0.93
2.00
2.18
7.15
7.17
7.48
7.52
7.54
38
N-(4-Nitrophenyl)acetamide(3r): H1 NMR & C13 NMR
N-
39
(Pyridin-2-yl)acetamide(3s): H1 NMR
-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.5f1 (ppm)
3.06
1.17
0.98
1.01
1.00
0.92
2.20
7.26
7.27
7.28
7.29
8.18
8.20
8.31
8.32
8.58
8.59
8.74
N-(4-Bromopyridin-2-yl)acetamide(3t): H1 NMR & C13 NMR
40
N-(Pyridin-3-yl)acetamide(3u): H1 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.09.510.0f1 (ppm)
3.20
1.02
1.03
2.00
1.00
2.21
7.03
7.03
7.04
7.04
7.05
7.05
7.06
7.06
7.72
7.72
7.74
7.74
8.23
8.25
8.26
8.27
8.28
8.28
9.36
41
N-(2-(Diethylamino)ethyl)-4-nitrobenzamide: H1 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)
6.08
4.09
2.07
2.04
2.00
2.00
1.11
1.13
1.14
2.71
2.73
2.75
2.76
2.83
2.84
2.85
3.60
3.61
3.62
3.64
8.00
8.02
8.23
8.26
Procainamide: H1 NMR & C13 NMR
0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.59.0f1 (ppm)
6.09
4.01
2.00
2.05
2.09
2.03
0.86
1.38
1.40
1.42
3.43
3.44
3.46
3.48
3.49
3.50
3.52
3.81
3.82
6.70
6.72
7.69
7.71
8.38
42
0102030405060708090100110120130140150160170180190200210220f1 (ppm)
9.53
37.5
8
49.1
9
56.0
0
114.
03
120.
76
130.
20
153.
60
171.
30
