The Journal of Organic Chemistry
Page 14 of 17
1
2
3
4
5
1-(naphthalen-1-yl) pyridin-1-ium chloride (2o).40 2o was prepared from 1o (85.9 mg, 0.6 mmol, 3 eq) after 20 min
of heating under microwaves at 150 °C, and purified according to method 1. 2o was obtained under the form of a very
6
7
1
hygroscopic red solid (33.7 mg, 70%). H NMR (400 MHz, MeOH-d4) δ 9.29 – 9.23 (m, 2H), 8.93 (tt, J = 7.9, 1.4
8
9
Hz, 1H), 8.39 (dd, J = 7.8, 6.7 Hz, 2H), 8.32 (d, J = 8.4 Hz, 1H), 8.21 – 8.15 (m, 1H), 7.92 (dd, J = 7.4, 1.1 Hz, 1H),
7.82 – 7.67 (m, 3H), 7.39 – 7.35 (m, 1H). 13C NMR (100 MHz, MeOH-d4) δ 148.8, 147.9, 140.4, 135.6, 133.4, 130.4,
129.9, 129.8, 129.1, 128.4, 126.5, 125.5, 121.3. IR (neat) ν 3364, 3034, 1509, 1469, 774, 684. LC-MS m/z (%) 206
(100), 207 (15). Anal calcd for C15H12ClN.H2O: C, 69.36; H, 5.43; N, 5.39. Found: C, 69.49; H, 5.38; N, 5.41.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
1-(3-hydroxyphenyl)pyridin-1-ium chloride (2p). 2p was prepared from 1p (43.6 mg, 0.4 mmol, 2 eq) after 40 min
of heating under microwaves at 130 °C, and purified according to method 2. 2p was obtained under the form of a
very hygroscopic black solid (26.4 mg, 63%). 1H NMR (400 MHz, MeOH-d4) δ 9.22 (d, 2H, J = 6.5Hz), 8.78 (t, 1H,
J = 6.5 Hz), 8.27 (t, 2H, J = 6.5 Hz), 7.54 (t, 1H, J = 9.8 Hz), 7.24 (d, 1H, J = 9.8 Hz), 7.22 (s, 1H), 7.15 (d, 1H, J =
9.8 Hz). 13C NMR (100 MHz, MeOH-d4) δ 160.6, 147.9, 146.0, 145.5, 132.6, 129.5, 119.6, 115.9, 112.4. IR (neat) ν
= 3485, 3047, 3026, 1567, 1480, 1335, 1297, 1252, 805, 794. LC-MS m/z (%) 172 (100), 173 (13), 343 (17).
Anal calcd for C11H10ClNO.2H2O: C, 54.22; H, 5.79; N, 5.75. Found: C, 54.59; H, 5.88; N, 5.59.
1-(o-tolyl)pyridin-1-ium chloride (2q).40 2q was prepared from 1q (42.8 mg, 0.4 mmol, 2 eq) after 15 min of heating
under microwaves at 130 °C, and purified according to method 2. 2q was obtained under the form of a brown powder
(38.9 mg, 94%). 1H NMR (400 MHz, MeOH-d4) δ 9.13 (dd, 2H, J = 6.7, 1.3 Hz), 8.86 (tt, 1H, J = 6.7, 1.3 Hz), 8.34
(t, 2H, J = 6.7 Hz, 7.68-7.53 (bp, 4H), 2.21 (s, 3H). 13C NMR (100 MHz, MeOH-d4) δ 148.3, 147.3, 143.8, 133.9,
133.2, 132.9, 129.7, 129.0, 126.9, 17.0. IR (neat) ν 3365, 3118, 2923, 1487, 1469, 1385, 767, 717, 685. LC-MS m/z
(%) 170 (100), 171 (13). Anal calcd for C12H12ClN.7/4H2O: C, 60.76; H, 6.59; N, 5.90. Found: C, 60.93; H, 6.28; N,
5.99.
1-(2-methoxyphenyl)pyridin-1-ium chloride (2r).40 2r was prepared from 1r (49.3 mg, 0.4 mmol, 2 eq) after 30 min
of heating under microwaves at 130 °C, and purified according to method 2. 2r was obtained under the form of a light
brown powder (35.5 mg, 80%). 1H NMR (400 MHz, DMSO-d6) δ 9.24 (dd, 2H, J = 6.5, 1.2 Hz), 8.81 (tt, 1H, J = 6.5,
1.2 Hz), 8.32 (t, 2H, J = 6.5 Hz), 7.77 (d, 1H, J = 7.9 Hz), 7.72 (t, 1H, J = 7.9 Hz), 7.46 (d, 1H, J = 7.9 Hz), 7.28 (t,
1H, J = 7.9 Hz), 3.86 (s, 3H). 13C NMR (100 MHz, DMSO-d6) δ 151.8, 147.1, 146.7, 133.0, 131.2, 127.9, 126.9,
121.2, 113.4, 56.6. IR (neat) ν 3440, 3380, 3031, 2841, 1606, 1440, 1277, 1020, 763, 684, 694. LC-MS m/z (%) 186
(100), 187 (17). Anal calcd for C12H12ClNO.4/3H2O: C, 58.66; H, 6.02; N, 5.70. Found: C, 58.82; H, 5.66; N, 5.86.
1-phenylpyridin-1-ium chloride (2s).36 2s was prepared from 1s (22.3 mg, 0.24 mmol, 1.2 eq) after 20 min of heating
under microwaves at 130 °C, and purified according to method 2. 2s was obtained under the form of a brown powder
(38.3 mg, 100%). 1H NMR (400 MHz, DMSO-d6) δ 9.37 (d, 2H,J = 7.1 Hz), 8.79 (t, 1H, J = 7.1 Hz), 8.32 (t, 2H, J =
7.1 Hz), 7.90 (dd, 2H, J = 5.9, 1.9 Hz), 7.75 (bp, 3H). 13C NMR (100 MHz, DMSO-d6) δ 146.6, 145.0, 142.8, 131.2,
ACS Paragon Plus Environment