The Journal of Organic Chemistry
Article
δ 10.02 (s, 1H), 8.70 (dd, J = 6.8, 1.4 Hz, 1H), 8.57 (d, J = 6.8 Hz,
1H), 8.47 (dd, J = 8.3, 1.1 Hz, 1H), 8.34 (dd, J = 8.3, 1.0 Hz, 1H),
8.25 (ddd, J = 8.3, 7.0, 1.2 Hz, 1H), 8.06 (ddd, J = 8.3, 6.9, 1.2 Hz,
1H), 4.48 (s, 3H).
6-(4-Chlorophenyl)-2-methylisoquinolin-2-ium Iodide (A37)
(General Procedure A). Bright yellow solid (yield: 1.70 g, 89%).
mp 286−287 °C. H NMR (400 MHz, DMSO-d6) δ 9.97 (s, 1H),
8.69 (d, J = 6.9 Hz, 2H), 8.54 (t, J = 7.1 Hz, 2H), 8.41 (dd, J = 8.7,
1.7 Hz, 1H), 8.05−7.98 (m, 2H), 7.74−7.65 (m, 2H), 4.47 (s, 3H).
13C{1H} NMR (101 MHz, DMSO-d6) δ 150.7, 146.5, 137.6, 136.9,
136.8, 135.2, 131.3, 130.4, 130.0, 129.9, 126.7, 125.9, 124.8, 48.3.
HRMS (ESI) m/z: calcd for C16H13ClN [M]+ 254.0731, found
254.0730.
6-([1,1′-Biphenyl]-4-yl)-2-methylisoquinolin-2-ium Iodide (A38)
(General Procedure A). Yellowish solid (yield: 1.79 g, 85%). mp
275−276 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.97 (s, 1H), 8.77−
8.64 (m, 2H), 8.58−8.52 (m, 2H), 8.48 (dd, J = 8.7, 1.4 Hz, 1H), 8.09
(d, J = 8.4 Hz, 2H), 7.92 (d, J = 8.4 Hz, 2H), 7.79 (d, J = 7.3 Hz, 2H),
7.52 (t, J = 7.6 Hz, 2H), 7.43 (t, J = 7.3 Hz, 1H), 4.47 (s, 3H).
13C{1H} NMR (101 MHz, DMSO-d6) δ 150.5, 147.3, 141.8, 139.4,
137.6, 136.97, 136.7, 131.3, 130.4, 129.5, 128.8, 128.5, 128.0, 127.2,
126.6, 125.8, 124.4, 48.3. HRMS (ESI) m/z: calcd for C22H18N [M]+
296.1434, found 296.1435.
2-Methyl-6-(4-(trifluoromethyl)phenyl)isoquinolin-2-ium Iodide
(A39)10 (General Procedure A). Yellow solid (yield: 1.76 g, 85%).
1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 8.77−8.70 (m, 2H),
8.59 (t, J = 7.2 Hz, 2H), 8.46 (dd, J = 8.7, 1.7 Hz, 1H), 8.19 (d, J =
8.1 Hz, 2H), 7.99 (d, J = 8.3 Hz, 2H), 4.49 (s, 3H).
1
2,6-Dimethylisoquinolin-2-ium Iodide (A27)10 (General Proce-
1
dure A). Yellow solid (yield: 1.30 g, 90%). H NMR (400 MHz,
DMSO-d6) δ 9.89 (s, 1H), 8.63 (dd, J = 6.7, 1.4 Hz, 1H), 8.43 (d, J =
6.8 Hz, 1H), 8.37 (d, J = 8.5 Hz, 1H), 8.12 (s, 1H), 7.92 (dd, J = 8.5,
1.6 Hz, 1H), 4.44 (s, 3H), 2.66 (s, 3H).
6-Cyclopropyl-2-methylisoquinolin-2-ium Iodide (A28)10 (Gen-
1
eral Procedure A). Yellow solid (yield: 1.24 g, 80%). H NMR (400
MHz, DMSO-d6) δ 9.82 (s, 1H), 8.58 (dd, J = 6.8, 1.2 Hz, 1H),
8.37−8.30 (m, 2H), 8.01 (s, 1H), 7.76 (dd, J = 8.7, 1.6 Hz, 1H), 4.41
(s, 3H), 2.34−2.23 (m, 1H), 1.29−1.20 (m, 2H), 1.05−0.99 (m, 2H).
6-Methoxy-2-methylisoquinolin-2-ium Iodide (A29)10 (General
Procedure A). Yellow solid (yield: 1.28 g, 84%). 1H NMR (400 MHz,
DMSO-d6) δ 9.77−9.72 (m, 1H), 8.55 (dd, J = 6.8, 1.5 Hz, 1H),
8.39−8.29 (m, 2H), 7.74 (d, J = 2.5 Hz, 1H), 7.64 (dd, J = 9.1, 2.5
Hz, 1H), 4.37 (s, 3H), 4.04 (s, 3H).
6-Chloro-2-methylisoquinolin-2-ium Iodide (A30)10 (General
Procedure A). Yellow solid (yield: 1.11 g, 73%). 1H NMR (400
MHz, DMSO-d6) δ 10.04 (s, 1H), 8.75 (d, J = 6.8 Hz, 1H), 8.55−
8.49 (m, 3H), 8.11 (dd, J = 8.8, 2.1 Hz, 1H), 4.47 (s, 3H).
6-Bromo-2-methylisoquinolin-2-ium Iodide (A31)10 (General
Procedure A). Yellow solid (yield: 1.10 g, 62%). 1H NMR (400
MHz, DMSO-d6) δ 10.02 (s, 1H), 8.77−8.67 (m, 2H), 8.49 (d, J =
6.8 Hz, 1H), 8.42 (d, J = 8.8 Hz, 1H), 8.22 (dd, J = 8.8, 1.9 Hz, 1H),
4.45 (s, 3H).
6-(2-Fluorophenyl)-2-methylisoquinolin-2-ium Iodide (A40)
(General Procedure A). Yellowish solid (yield: 1.50 g, 82%). mp
1
293−294 °C. H NMR (400 MHz, DMSO-d6) δ 10.03 (s, 1H), 8.73
2-Methyl-6-phenylisoquinolin-2-ium Iodide (A32)10 (General
Procedure A). Yellow solid (yield: 1.21 g, 70%). 1H NMR (400
MHz, DMSO-d6) δ 9.98 (d, J = 6.7 Hz, 1H), 8.68 (d, J = 10.6 Hz,
2H), 8.57−8.53 (m, 2H), 8.43 (dd, J = 8.7, 1.7 Hz, 1H), 7.98 (d, J =
7.1 Hz, 2H), 7.67−7.52 (m, 3H), 4.47 (s, 3H).
(d, J = 6.7 Hz, 1H), 8.62−8.53 (m, 3H), 8.26 (d, J = 8.5 Hz, 1H),
7.79 (td, J = 7.8, 1.5 Hz, 1H), 7.65−7.56 (m, 1H), 7.50−7.43 (m,
2H), 4.49 (s, 3H). 13C{1H} NMR (101 MHz, DMSO-d6) δ 159.7 (d,
J = 248.3 Hz), 150.9, 143.2, 137.2, 136.8, 132.3 (d, J = 3.2 Hz), 132.2,
131.8 (d, J = 2.5 Hz), 130.9, 127.3 (d, J = 3.5 Hz), 126.7 (d, J = 2.0
Hz), 126.6, 125.9, 125.9, 117.0 (d, J = 22.2 Hz), 48.4. HRMS (ESI)
m/z: calcd for C16H13FN [M]+ 238.1027, found 238.1025.
6-(4-Ethoxyphenyl)-2-methylisoquinolin-2-ium Iodide (A33)
(General Procedure A). Yellowish solid (yield: 1.55 g, 82%). mp
1
289−290 °C. H NMR (400 MHz, DMSO-d6) δ 9.92 (s, 1H), 8.64
6-(3-Cyanophenyl)-2-methylisoquinolin-2-ium Iodide (A41)
(General Procedure A). Bright yellow solid (yield: 1.26 g, 68%).
mp 288 °C. 1H NMR (400 MHz, DMSO-d6) δ 10.02 (s, 1H), 8.77 (s,
1H), 8.72 (dd, J = 6.8, 1.2 Hz, 1H), 8.57 (dd, J = 15.4, 7.8 Hz, 2H),
8.47 (dd, J = 8.5, 1.6 Hz, 2H), 8.34−8.29 (m, 1H), 8.05−8.00 (m,
1H), 7.82 (t, J = 7.9 Hz, 1H), 4.50 (s, 3H). 13C{1H} NMR (101
MHz, DMSO-d6) δ 150.8, 145.5, 139.3, 137.4, 136.9, 133.5, 133.0,
131.9, 131.4, 131.1, 130.4, 126.9, 126.0, 125.5, 118.9, 113.0, 48.4.
HRMS (ESI) m/z: calcd for C17H13N2 [M]+ 245.1073, found
245.1076.
(dd, J = 6.8, 1.0 Hz, 1H), 8.59 (s, 1H), 8.48 (d, J = 7.8 Hz, 2H), 8.39
(dd, J = 8.8, 1.6 Hz, 1H), 7.94 (d, J = 8.8 Hz, 2H), 7.14 (d, J = 8.8 Hz,
2H), 4.45 (s, 3H), 4.13 (q, J = 7.0 Hz, 2H), 1.37 (t, J = 7.0 Hz, 3H).
13C{1H} NMR (101 MHz, DMSO-d6) δ 160.5, 150.2, 147.5, 137.7,
136.5, 131.1, 130.1, 129.9, 129.6, 126.1, 125.5, 123.2, 115.8, 63.8,
48.1, 15.0. HRMS (ESI) m/z: calcd for C18H18NO [M]+ 264.1383,
found 264.1379.
2-Ethyl-6-(p-tolyl)isoquinolin-2-ium Iodide (A34) (General Pro-
1
cedure A). Yellowish solid (yield: 1.60 g, 85%). mp 248−249 °C. H
NMR (400 MHz, DMSO-d6) δ 9.95 (s, 1H), 8.70−8.62 (m, 2H),
8.52 (d, J = 7.8 Hz, 2H), 8.41 (dd, J = 8.7, 1.4 Hz, 1H), 7.91 (d, J =
8.2 Hz, 2H), 7.46 (d, J = 8.1 Hz, 2H), 4.46 (s, 3H), 2.71 (q, J = 7.5
Hz, 2H), 1.24 (t, J = 7.6 Hz, 3H). 13C{1H} NMR (101 MHz, DMSO-
d6) δ 150.5, 147.8, 146.3, 137.7, 136.6, 135.4, 131.2, 130.4, 129.3,
128.2, 126.5, 125.7, 124.1, 48.2, 28.3, 15.9. HRMS (ESI) m/z: calcd
for C18H18N [M]+ 248.1434, found 248.1426.
2-Methyl-6-(3-nitrophenyl)isoquinolin-2-ium Iodide (A42) (Gen-
eral Procedure A). Yellow solid (yield: 1.18 g, 60%). mp 275−277 °C.
1H NMR (400 MHz, DMSO-d6) δ 10.03 (s, 1H), 8.83 (s, 1H), 8.76−
8.71 (m, 1H), 8.61 (d, J = 5.8 Hz, 1H), 8.59 (d, J = 3.8 Hz, 1H), 8.51
(dd, J = 8.7, 1.7 Hz, 1H), 8.46−8.42 (m, 1H), 8.42−8.37 (m, 1H),
7.92 (t, J = 8.0 Hz, 1H), 4.50 (s, 3H). 13C{1H} NMR (101 MHz,
DMSO-d6) δ 150.9, 149.0, 145.3, 139.8, 137.5, 136.9, 134.7, 131.5,
130.5, 127.0, 126.1, 125.7, 124.6, 122.8, 48.4. HRMS (ESI) m/z:
calcd for C16H13N2O2 [M]+ 265.0972, found 265.0971.
6-(4-(tert-Butyl)phenyl)-2-methylisoquinolin-2-ium Iodide (A35)
(General Procedure A). Bright yellow solid (yield: 1.61 g, 80%). mp
201−202 °C. 1H NMR (400 MHz, DMSO-d6) δ 9.95 (s, 1H), 8.69−
8.61 (m, 2H), 8.53 (d, J = 7.7 Hz, 2H), 8.41 (dd, J = 8.8, 1.7 Hz, 1H),
7.95−7.89 (m, 2H), 7.66−7.60 (m, 2H), 4.46 (s, 3H), 1.35 (s, 9H).
13C{1H} NMR (101 MHz, DMSO-d6) δ 153.0, 150.4, 147.7, 137.6,
136.6, 135.2, 131.2, 130.4, 128.0, 126.7, 126.5, 125.7, 124.1, 48.2,
35.0, 31.4. HRMS (ESI) m/z: calcd for C20H22N [M]+ 276.1747,
found 276.1744.
2-Methyl-6-(naphthalen-2-yl)isoquinolin-2-ium Iodide (A43)10
1
(General Procedure A). Yellow solid (yield: 1.15 g, 58%). H NMR
(400 MHz, DMSO-d6) δ 10.12 (s, 1H), 8.76 (dd, J = 6.7, 0.9 Hz,
1H), 8.61 (d, J = 7.7 Hz, 2H), 8.49 (s, 1H), 8.20 (dd, J = 8.5, 1.5 Hz,
1H), 8.10 (t, J = 7.4 Hz, 2H), 7.78 (d, J = 8.3 Hz, 1H), 7.72−7.67 (m,
1H), 7.66−7.59 (m, 2H), 7.58−7.53 (m, 1H), 4.53 (s, 3H).
2-Methyl-6-(pyren-1-yl)isoquinolin-2-ium Iodide (A44) (General
Procedure A). Saffron solid (yield: 1.22 g, 52%). mp 292−294 °C. 1H
NMR (400 MHz, DMSO-d6) δ 10.09 (s, 1H), 8.74 (dd, J = 6.8, 1.1
Hz, 1H), 8.64 (d, J = 8.6 Hz, 1H), 8.61 (d, J = 5.3 Hz, 2H), 8.47 (d, J
= 7.9 Hz, 1H), 8.40 (d, J = 7.6 Hz, 1H), 8.34 (t, J = 7.4 Hz, 2H), 8.31
(t, J = 4.6 Hz, 2H), 8.25 (d, J = 9.4 Hz, 1H), 8.18 (d, J = 7.9 Hz, 1H),
8.14 (t, J = 7.6 Hz, 1H), 8.09 (d, J = 9.3 Hz, 1H), 4.53 (s, 3H).
13C{1H} NMR (101 MHz, DMSO-d6) δ 150.8, 148.8, 137.2, 136.7,
6-(4-Fluorophenyl)-2-methylisoquinolin-2-ium Iodide (A36)
(General Procedure A). Yellowish solid (yield: 1.53 g, 84%). mp
1
154−155 °C. H NMR (400 MHz, DMSO-d6) δ 9.99 (s, 1H), 8.69
(dd, J = 6.8, 0.9 Hz, 1H), 8.65 (s, 1H), 8.53 (d, J = 7.8 Hz, 2H), 8.39
(dd, J = 8.8, 1.6 Hz, 1H), 8.11−7.97 (m, 2H), 7.51−7.35 (m, 2H),
4.48 (s, 3H). 13C{1H} NMR (101 MHz, DMSO-d6) δ 163.6 (d, J =
247.9 Hz), 150.6, 146.7, 137.6, 136.7, 134.6 (d, J = 3.0 Hz), 131.3,
130.6 (d, J = 8.7 Hz), 130.4, 126.5, 125.8, 124.5, 116.8 (d, J = 21.8
Hz), 48.3. HRMS (ESI) m/z: calcd for C16H13FN [M]+ 238.1027,
found 238.1025.
134.9, 134.1, 131.7, 131.3, 130.7, 130.7, 129.2, 128.8, 128.6, 128.4,
128.0, 127.8, 127.2, 126.6, 126.5, 126.0, 125.9, 125.6, 124.5, 124.2,
I
J. Org. Chem. XXXX, XXX, XXX−XXX