6
F. Shirini et al. / Journal of Molecular Liquids xxx (2014) xxx–xxx
Scheme 2. Synthesis of the ionic liquid from 3-methyl imidazole.
(m, 8H); 13C NMR (CDCl3, 100 MHz) ppm: 23.4, 52.62, 125.1, 238
125.9, 127.9, 128.6, 128.9, 129.1, 130.4, 131.1, 132.5, 134.9, 145.6, 239
t1:1
t1:2
t1:3
Table 1
The effect of different amounts of C4(mim)2-2Br−-2H2SO4 on the reaction of 2-amino
benzophenone with acetyl acetone.a
146.1, 154.8, 168.7.
240
t1:4
Entry
Catalyst (mmol)
Time (min)
Yield (%)b
Ethyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate (l):
241
M. p. 98–100 °C. IR (KBr) ν cm−1: 3042, 2936, 1712; 1HNMR(CDCl3, 242
400 MHz) ppm: 0.90 (t, J = 7.0 Hz, 3H), 2.73 (s, 3H), 3.88 (q, J = 243
7.0 Hz, 2H), 7.30–7.47 (m, 6H), 7.51 (dd, J1 = 8.8 Hz, J2 = 2.4, 244
1H), 7.88 (d, J = 8.8 Hz, 1H); 13C NMR (CDCl3, 100 MHz) ppm: 245
13.5, 23.8, 59.9, 124.5, 125.8, 127.9, 128.4, 128.2, 128.9, 130.1, 246
t1:5
t1:6
t1:7
t1:8
1
2
3
4
0.01
0.03
0.05
0.07
60
40
25
25
80
86
93
94
a
t1:9
Reaction conditions: 2-aminobenzophenone (1 mmol), acetyl acetone (1.2 mmol),
50 °C under solvent-free conditions.
b
t1:10
Isolated yield.
130.8, 132.2, 134.6, 144.9, 145.4, 154.7, 167.8.
6-(Chloro-2-methyl-4-phenylquinolin-3-yl)(phenyl)methanone 248
(m): 249
247
M. p. 209–211 °C. IR (KBr) ν cm−1: 2925, 2851, 1680, 1240; 1H NMR 250
(CDCl3, 400 MHz) ppm: 2.49 (s, 3H), 7.12 (m, 7H), 7.41 (m, 1H), 7.46 251
(m, 3H), 7.66 (d, J = 2.40 Hz, 1H), 7.96 (d, J = 8.8 Hz, 1H). 13C NMR 252
(CDCl3, 100 MHz) ppm: 23.8, 124.7, 125.9, 128.1, 128.3, 128.4, 129.0, 253
129.7, 130.4, 130.8, 132.3, 133.0, 133.5, 133.9, 136.7, 144.6, 146.0, 254
217
218
219
220
221
222
223
224
225
226
227
228
229
230
3.27 (t, J = 7.6 Hz, 2H), 7.37–7.43 (m, 3H), 7.48–7.56 (m, 3H), 7.62–
7.66 (m, 2H), 8.07–8.09 (m, 1H); 13C NMR (CDCl3, 100 MHz) ppm:
24.0, 29.9, 35.3, 124.9, 125.7, 126.4, 128.6, 128.3, 129.3, 133.7,
137.0, 142.5, 148.0, 167.6.
6-Phenyl-7H-indeno[1,2-b]quinolin-7-one (i):
1.1. M. p. 180–182 °C. IR (KBr) ν cm−1: 3074, 2929, 1621, 1455;
(CDCl3, 400 MHz) ppm: 7.44 (t, J = 8.0 Hz, 2H), 7.50–7.59 (m, 4H),
7.60–7.74 (t, J = 8.0 Hz, 3H), 7.81–7.85 (t, J = 8.0 Hz, 1H), 8.32
(s, 2H) 13C NMR (CDCl3, 100 MHz) ppm: 29.7, 123.0, 124.1,
127.0, 127.7, 128.1, 128.7, 128.9, 129.3, 131.7, 140.0, 133.0,
135.4, 137.7, 163.1.
154.8, 199.9.
255
7-Chloro-9-phenyl-3,4-dihydro-1-2H-acridinone (n):
256
M. p. 187–189 °C. IR (KBr) ν cm−1: 3032, 2967, 2875, 1688, 257
1549. 1HNMR (CDCl3, 400 MHz) ppm: 2.24 (q, J = 6.4 Hz, 2H), 258
2.70 (t, J = 6.4 Hz, 2H), 3.32 (t, J = 6.4 Hz, 2H), 7.15 (t, 2H), 7.41 259
(s, H), 7.52 (m, 3H), 7.59 (d, J = 8.4 Hz, 1H,), 7.98 (d, J = 8.4 Hz, 260
1H); 13C NMR (CDCl3, 100 MHz) ppm: 20.9, 34.2, 40.3, 124.2, 261
1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)ethanone (j):
M.p. 159–160 °C. IR (KBr) ν cm−1: 3056, 2938, 1675 cm−1
;
126.3, 127.8, 130.0, 132.2, 136.6, 146.7, 149.9, 162.2, 197.0.
262
1HNMR(CDCl3, 400 MHz) ppm: 1.94 (s, 3H), 2.68 (s, 3H), 7.31–
7.34 (m, 2H), 7.49–7.56 (m, 4H), 7.60–7.64 (m, 1H), 7.99 (d, J =
9.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz) ppm: 23.5, 31.9, 124.6,
125.8, 128.7, 129.2, 129.7, 130.2, 130.6, 132.4, 134.5, 135.6, 143.1,
145.6, 153.9, 205.0.
7-Chloro-3,3-dimethyl-9-phenyl-3,4-dihydro-2H-acridin-1-one (o): 263
M. p. 207–209 °C. IR (KBr) ν cm−1: 3071, 2946, 1693; 1HNMR 264
(CDCl3, 400 MHz) ppm: 1.12 (s, 6H), 2.53 (s, 2H), 3.25 (s, 2H), 265
7.13–7.16 (m, 2H), 7.28 (d, J = 2.4 Hz, 1H), 7.42–7.55 (m, 3H), 266
7.71 (dd, J1 = 8.8 Hz, J2 = 2.8 Hz, 1H), 8.05 (d, J = 8.8 Hz, 1H); 267
13C NMR (CDCl3, 100 MHz) ppm: 28.4, 32.3, 48.4, 54.3, 123.5, 268
126.8, 127.7, 127.9, 128.1, 128.2, 130.0, 132.3, 132.5, 136.8, 147.2, 269
231
232
233
234
235
236
237
Methyl 6-chloro-2-methyl-4-phenylquinoline-3-carboxylate (k):
M. p. 131–133 °C; IR (KBr) ν cm−1: m 3063, 2945, 1735; 1H
NMR(CDCl3, 400 MHz) ppm: 2.56 (s, 3H), 3.54 (s, 3H), 7.26–7.92
150.2, 161.2, 197.5.
270
Scheme 3. Friedländer reaction in the presence of C4(mim)2-2Br−-2H2SO4 as the catalyst.