ACCEPTED MANUSCRIPT
N, N-dimethyl-4-cyanobenzamide (3f).Yield: 85 %. 1H NMR (300 MHz, CDCl3) δ 7.72-7.67 (m, 2H), 7.53-7.47 (m, 2H),
13
3.11 (s, 3H), 2.94 (s, 3H)ꢀ C NMR (75 MHz, CDCl3) δ 169.6, 140.7, 132.4, 127.8, 118.2, 113.4, 39.4, 35.4; MS (70eV, EI) m/z
(EI) C10H10N2O [M]: 174.19, 75 (53), 102 (100), 130 (45), 173 (33), 174 (6).
N, N-dimethyl-2-chlorobenzamide (3g). Yield: 89 %. 1H NMR (300 MHz, CDCl3) δ 7.35-7.19 (m, 4H), 3.07 (s, 3H), 2.80 (s,
3H); 13C NMR (75 MHz, CDCl3) δ 168.5, 136.4, 130.2 (d, J = 14.4 Hz), 129.6, 127.8, 127.2, 38.1, 34.7; MS (70eV, EI) m/z (EI)
C9H10ClNO [M]: 183.63, 75 (100), 111 (84), 139 (59), 182 (16), 184 (6).
N, N-dimethyl-2-nitrobenzamide (3h).Yield: 85 %. 1H NMR (300 MHz, CDCl3) δ 8.20 (dd, J = 8.3, 1.0 Hz, 1H), 7.74-7.69
(m, 1H), 7.59-7.54 (m, 1H), 7.41 (dd, J = 7.5, 1.3 Hz, 1H), 3.17 (s, 3H), 2.84 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 168.1, 145.1,
134.7, 133.3, 129.8, 128.2, 124.8, 38.3, 35.0; MS (70eV, EI) m/z (EI) C9H10N2O3 [M]: 194.19, 63 (87), 78 (100), 150 (75),195
(84).
N, N-dimethyl-2-(trifluoromethyl)benzamide (3i). Yield: 59 %. 1H NMR (300 MHz, CDCl3) δ 7.70 (d, J = 7.8 Hz, 1H), 7.62
(dd, J = 5.9, 3.4 Hz, 1H), 7.51 (t, J = 7.7 Hz, 1H), 7.35 (d, J = 7.5 Hz, 1H), 3.14 (s, 3H), 2.80 (s, 3H); 13C NMR (75 MHz, CDCl3)
δ 169.1, 135.4 (d, J = 2.2 Hz), 132.3 (d, J = 0.8 Hz), 129.1, 127.4, 126.7 (d, J = 4.6 Hz), 38.9, 34.9; MS (70eV, EI) m/z (EI)
C10H10F3NO [M]: 217.19, 75 (33), 95 (37), 145 (63), 173 (61), 216 (100), 217 (14).
N, N-dimethyl-3-nitrobenzamide (3j).Yield: 85 %. 1H NMR (300 MHz, CDCl3) δ 8.32-8.23 (m, 2H), 7.76 (dt, J = 7.6, 1.3 Hz,
1H), 7.65-7.58 (m, 1H), 3.14 (s, 3H), 3.00 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 169.1, 148.1, 137.9, 133.3, 129.8, 124.5, 122.4,
39.7, 35.7; MS (70eV, EI) m/z (EI) C9H10N2O3 [M]: 194.19, 76 (63), 92 (25), 104 (100), 150 (21), 177 (6), 193 (10), 194 (3).
N, N-dimethyl-2-naphthamide (3k).Yield: 60 %. 1H NMR (300 MHz, CDCl3) δ 7.91 (s, 1H), 7.89-7.83 (m, 3H), 7.52 (m, J =
8.5, 4.1, 2.1 Hz, 3H), 3.16 (s, 3H), 3.03 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 171.8, 133.7 (d, J = 2.2 Hz), 132.8, 128.4 (d, J =
15.6 Hz), 127.9, 127.2 -126.6 (m), 124.5, 39.8, 35.6; MS (70eV, EI) m/z (EI) C13H13NO [M]: 199.25, 77 (76), 127 (100), 155
(10), 198 (15), 199 (8).
N, N-dimethyl-3-methyl-2-nitrobenzamide (3l). Yield: 26 %. 1H NMR (300 MHz, CDCl3) δ 7.45 (t, J = 7.6 Hz, 1H), 7.34 (d,
J = 7.7 Hz, 1H), 7.21 (d, J = 6.7 Hz, 1H), 3.10 (s, 3H), 2.94 (s, 3H), 2.47 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.1, 145.7,
135.9, 134.9, 127.0, 124.4, 122.1, 34.2, 17.6; MS (70eV, EI) m/z(EI) C10H12N2O3 [M]: 208.21, 65 (100), 77 (22), 89 (43), 119
(9), 209 (5).
N, N-dimethyl-2-chloro-5-nitrobenzamide (3m). Yield: 35 %. 1H NMR (300 MHz, CDCl3) δ 8.19 (dd, J=7.3, 2.5 Hz, 2H),
7.62-7.57 (m, 1H), 3.17 (s, 3H), 2.90 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 137.5, 130.9, 124.9, 123.4, 38.2, 34.9; MS (70eV, EI)
m/z(EI) C9H9ClN2O3 [M]: 228.63, 75 (100), 110 (18), 138 (6), 229 (11).
N, N-dimethyl-4-chloro-2-nitrobenzamide (3n).Yield: 37 %. 1H NMR (300 MHz, CDCl3) δ 8.20 (d, J = 2.0 Hz, 1H), 7.69
(dd, J = 8.2, 2.0 Hz, 1H), 7.36 (d, J = 8.2 Hz, 1H), 3.16 (s, 3H), 2.84 (s, 3H); 13C NMR (75MHz, CDCl3) δ 167.1, 135.8, 134.7,
131.8, 129.4, 125.1, 38.4, 35.1; MS (70eV, EI) m/z(EI) C9H9ClN2O3 [M]: 228.63, 76 (100), 110 (5), 184 (5), 229 (19).
N, N-dimethylnicotinamide (3o). Yield: 68 %. 1H NMR (300 MHz, CDCl3) δ 8.76-8.60 (m, 2H), 7.77 (dt, J = 7.8, 1.9 Hz, 1H),
7.36 (dd, J = 7.8, 4.9 Hz, 1H), 3.14 (s, 3H), 3.02 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 150.8, 148.2, 135.1, 123.5, 39.7, 35.6;
MS (70eV, EI) m/z (EI) C8H10N2O, [M]: 150.18, 50 (69), 51 (100), 73 (40), 78 (83), 149 (23), 150 (3).
N, N-dimethylpicolinamide (3p).Yield: 60 %. 1H NMR (300 MHz, CDCl3) δ 8.59 (d, J = 4.8 Hz, 1H), 7.79 (td, J=7.7, 1.7 Hz,
1H), 7.63 (d, J=7.8 Hz, 1H), 7.34 (ddd, J = 7.6, 4.9, 1.1 Hz, 1H), 3.14 (s, 3H), 3.08 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 154.6,
148.4, 137.2, 124.5, 123.7, 39.2, 35.9; MS (70eV, EI) m/z (EI) C8H10N2O [M]: 150.17, 79 (100), 93 (94), 121 (22), 150 (5).
N, N-dimethylisonicotinamide (3q). Yield: 79 %. 1H NMR (300 MHz, CDCl3) δ 8.70 (d, J = 4.9 Hz, 2H), 7.31 (d, J = 5.9 Hz,
2H), 3.12 (s, 3H), 2.95 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 169.0, 150.2, 144.3, 121.5, 39.3, 35.3; MS (70eV, EI) m/z (EI)
C8H10N2O, [M]: 150.18, 50 (67), 51 (100), 78 (66), 149 (6), 150 (1), 151 (4).
N, N-dimethylfuran-3-carboxamideamide (3r). Yield: 75 %.1H NMR (300 MHz, CDCl3) δ 7.72 (dd, J = 1.4, 0.8 Hz, 1H),
7.41 (t, J = 1.7 Hz, 1H), 6.61 (dd, J = 1.8, 0.8 Hz, 1H), 3.11 (s, 6H); 13C NMR (75 MHz, CDCl3) δ 164.9, 143.8, 142.8, 121.5,
110.6; MS (70eV, EI) m/z (EI) C7H9NO2, [M]: 139.06, 39 (51), 42 (17), 67 (24), 95 (41), 110 (45), 140 (100).
N, N-dimethylthiophene-3-carboxamde (3s). Yield: 82 %.1H NMR (300 MHz, CDCl3) δ 7.52 (dd, J = 2.9, 1.3 Hz, 1H), 7.31
(dd, J = 5.0, 2.9 Hz, 1H), 7.22 (dd, J = 5.0, 1.3 Hz, 1H), 3.08 (s, 6H);13C NMR (75 MHz, CDCl3) δ 166.9, 136.8, 127.38, 126.5,
125.7, 39.4, 35.6; MS (70eV, EI) m/z (EI) C7H9NOS, [M]: 155.04, 39 (62), 111 (52), 122 (36), 156 (100).
N, N-dimethylcinnamamide (3t). Yield: 90 %. 1H NMR (300 MHz, CDCl3) δ 7.67 (d, J = 15.5 Hz, 1H), 7.56 - 7.48 (m, 2H),
7.40 - 7.32 (m, 3H), 6.90 (d, J = 15.4 Hz, 1H), 3.11 (d, J = 30.4 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 166.7, 142.3, 135.4,
129.6, 128.8, 127.8, 117.5, 37.5, 35.9; MS (70eV, EI) m/z (EI) C11H13NO, [M]: 175.23, 51 (59), 77 (100), 103 (62), 131 (6), 175
(2).
6