642 Fan, Zhang, and Zhang
160.1; MS m/z(%): 347 (M++ 2), 345 (M+, 100).
Anal. calcd for C22H16ClNO: C 76.41, H 4.66, N 4.05;
found: C 76.43, H 4.68, N 4.03.
General Procedure for the Preparation
of 2,3,4-Trisubstituted Quinolines (5a–5d)
The preparative procedure of 2,3,4-trisubstituted
quinolines was very similar to what has been
previously described for the preparation of 2,4-
diarylquinolines. The following is the physical and
spectra data of the corresponding products.
6-Chloro-2-(4-methylphenyl)-4-(4-methoxyphe-
nyl)-quinoline 4g. mp 132–134◦C; IR ꢂ 3060, 1612,
1588 cm−1; 1H NMR (400 MHz, CDCl3) ꢁ 8.13 (d, 1H,
J = 8.8 Hz), 8.10 (d, 2H, J = 8.0 Hz), 7.89 (d, 1H,
J= 2.4 Hz), 7.79 (s, 1H), 7.66–7.62 (m, 1H), 7.48 (d,
2H, J = 8.8 Hz), 7.32 (d, 2H, J = 8.0 Hz), 7.09 (d,
2H, J = 8.8 Hz), 3.92 (s, 3H), 2.43 (s, 3H); 13C NMR
(100 MHz, CDCl3) ꢁ 21.4, 55.5, 114.3, 119.8, 124.6,
126.7, 127.4, 129.6, 130.2, 130.3, 130.7, 131.7, 131.9,
136.6, 139.7, 147.4, 148.1, 155.2; MS m/z (%): 361
(M++ 2), 359 (M+, 100). Anal. calcd for C23H18ClNO:
C 76.77, H 5.04, N 3.89; found: C 76.74, H 4.99, N
3.83.
6-Chloro-2-methyl-4-phenylquinoline
5a. mp
1
86–88◦C; IR ꢂ 3060, 3005, 1600 cm−1; H NMR (400
MHz, CDCl3) ꢁ 8.21 (d, 1H, J = 8.8 Hz), 7.91 (d, 1H,
J = 2.4 Hz), 7.88 (dd, 1H, J1 = 8.8 Hz, J2 = 2.4 Hz),
7.66–7.58 (m, 5H), 7.38 (s, 1H), 2.75 (s, 3H); 13C
NMR (100 MHz, CDCl3) ꢁ 20.8, 118.6, 121.1, 124.5,
124.8, 125.4, 125.8, 127.4, 135.2, 136.6, 146.3, 148.2,
158.4; MS m/z (%): 255 (M++ 2), 253 (M+, 100).
Anal. calcd for C16H12ClN: C 75.74, H 4.77, N 5.52;
found: C 75.78, H 4.69, N 5.55.
6-Chloro-2-(4-chlorophenyl)-4-(4-methoxyphe-
nyl)-quinoline 4h. mp 164–166◦C; IR ꢂ 3049, 1601,
1588 cm−1; 1H NMR (400 MHz, CDCl3) ꢁ 8.13 (d, 2H,
J = 8.4 Hz), 7.90 (d, 1H, J = 2.4 Hz), 7.77 (s, 1H),
7.67–7.65 (m, 1H), 7.51–7.47 (m, 5H), 7.10 (d, 2H,
J= 8.8 Hz), 3.93 (s, 3H); 13C NMR (100 MHz, CDCl3)
ꢁ 55.5, 114.4, 119.5, 124.7, 126.8, 128.8, 129.0, 130.6,
131.7, 132.4, 136.8, 137.7, 147.3, 148.5, 155.8, 160.2;
MS m/z (%): 383 (M++ 4), 381 (M++ 2), 379 (M+,
100). Anal. calcd for C22H15Cl2NO: C 69.49, H 3.98,
N 3.68; found: C 69.47, H 3.99, N 3.63.
6-Chloro-2,3-dimethyl-4-phenylquinoline
5b.
mp 123–125◦C; IR ꢂ 3050, 2982, 1610 cm−1; 1H
NMR (400 MHz, CDCl3) δ 8.12 (d, 1H, J = 8.4 Hz),
7.62–7.55 (m, 4H), 7.38 (d, 1H, J= 2.4 Hz), 7.28–7.25
(m, 2H), 2.82 (s, 3H), 2.16 (s, 3H); 13C NMR (100
MHz, CDCl3) ꢁ 16.1, 19.9, 120.9, 125.1, 126.5, 126.8,
127.4, 128.8, 129.1, 130.3, 133.4, 138.6, 145.3, 148.1,
160.2; MS m/z (%): 269 (M++ 2), 267 (M+, 100).
Anal. calcd for C17H14ClN: C 76.26, H 5.27, N 5.23;
found: C 76.32, H 5.31, N 5.22.
6-Chloro-2-(4-bromophenyl)-4-(4-methoxyphe-
nyl)-quinoline 4i. mp 175–177◦C; IR ꢂ 3038, 1600,
1578 cm−1; 1H NMR (400 MHz, CDCl3) ꢁ 8.14 (d, 1H,
J = 8.4 Hz), 8.10 (d, 2H, J = 8.4 Hz), 7.90 (d, 1H,
J = 2.2 Hz), 7.77 (s, 1H), 7.68–7.65 (m, 3H), 7.47
(d, 2H, J = 8.4 Hz), 7.10 (d, 2H, J = 8.4 Hz), 3.93
(s, 3H); 13C NMR (100 MHz, CDCl3) ꢁ 55.5, 114.4,
119.4, 124.2, 124.6, 126.8, 129.0, 129.8, 130.5, 130.7,
131.7, 132.0, 138.1, 147.8, 148.4, 155.8, 160.2; MS
m/z (%): 427 (M++ 4), 425 (M++ 2, 100), 423 (M+).
Anal. calcd for C22H15BrClNO: C 62.21, H 3.56, N
3.30; found: C 62.24, H 3.59, N 3.33.
6-Chloro-2-ethyl-3-methyl-4-phenylquinoline 5c.
mp 136–138◦C; IR ꢂ 3038, 2935, 1610 cm−1; 1H NMR
(400 MHz, CDCl3) ꢁ 8.02 (d, 1H, J = 8.4 Hz), 7.56–
7.47 (m, 4H), 7.22–7.27 (m, 3H), 3.06 (q, 2H, J = 7.2
Hz), 2.22 (s, 3H), 1.40 (t, 3H J = 7.2 Hz);13C NMR
(100 MHz, CDCl3) ꢁ 14.5, 19.2, 21.9, 120.6, 121.8,
124.9, 126.5, 126.8, 126.9, 127.8, 129.2, 129.4, 133.5,
139.2; 145.5, 147.2, 159.4; MS m/z (%): 283 (M++ 2),
281 (M+, 100). Anal. calcd for C18H16ClN: C 76.72, H
5.72, N 4.97; found: C 76.77, H 5.75, N 4.91.
6-Chloro-2,3-tetramethylene-4-phenylquinoline
5d . mp 166–168◦C; IR ꢂ 3050, 3000, 1621 cm−1;
1H NMR (400 MHz, CDCl3) ꢁ 8.11 (1H, d, J = 8.4
Hz), 7.60–7.53 (m, 4H), 7.30 (1H, d, J = 2.4 Hz),
7.25–7.22 (m, 2H), 3.20 (t, 2H, J = 7.2 Hz), 2.61 (t,
2H, J = 7.2 Hz), 2.03–1.97 (m, 2H), 1.85–1.80 (m,
2H); 13C NMR (100 MHz, CDCl3) ꢁ 24.8, 28.5, 32.6,
34.9, 121.6, 124.9, 125.6, 126.7, 126.8, 126.9, 127.9,
129.1, 129.2, 130.5, 133.9; 145.6, 148.2, 163.4; MS
m/z (%): 295 (M++ 2), 293 (M+, 100). Anal. calcd
for C19H16ClN: C 77.68, H 5.49, N 4.77; found: C
77.59, H 5.41, N 4.65.
6-Chloro-2-(4-bromophenyl)-4-(4-bromophenyl)-
quinoline 4j. mp 190–192◦C; IR ꢂ 3055, 1610, 1590
cm−1; 1H NMR (400 MHz, CDCl3) ꢁ 8.15 (d, 1H, J =
8.8 Hz), 8.06 (d, 2H, J = 8.4 Hz), 7.79–7.64 (m,
7H), 7.41 (d, 2H, J = 8.4 Hz); 13C NMR (100 MHz,
CDCl3) ꢁ 119.6, 125.3, 125.7, 129.6, 129.9, 131.3,
131.8, 133.6, 134.8, 135.1, 135.7, 139.6, 140.6, 150.2,
152.8, 161.6; MS m/z (%): 477 (M++ 6), 475 (M++
4), 473 (M++ 2, 100), 471 (M+). Anal. calcd for
C21H12Br2ClN: C 53.26, H 2.55, N 2.96; found: C
53.24, H 2.58, N 2.94.