Page 5 of 9
The Journal of Organic Chemistry
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58.1, 156.1, 146.9, 145.1, 140.7, 140.2, 140.1, 133.6,
31.1, 129.6, 128.8, 128.2, 128.0, 127.3, 125.8, 117.6,
146.9, 145.2, 141.8, 140.9, 133.9, 133.7, 132.0, 131.3,
129.6, 129.5, 129.4, 128.8, 127.8, 127.5, 127.3, 127.1,
126.1, 117.6, 103.6, 61.5, 61.0, 56.1, 42.1. HRMS
03.7, 61.5, 61.0, 56.0, 42.1. HRMS (ESI-TOF) m/z:
+
+
+
[(M+H)+] calcd for (C25
386.1756.
2-(4-chlorobenzyl)-3-(4-chlorophenyl)-5,6,7-
trimethoxyquinoline (Q2). Colorless oil (108mg,
96%). Isolated with 7.5% ethyl acetate in hexane. IR:
3060, 3026, 2917, 1600, 1585, 1493, 1073, 760, 695
H
24NO
3
) 386.1751; Found
(ESI-TOF) m/z: [(M+H) ] calcd for (C25
H
22Cl
2
NO
3
)
454.0971; Found 454.0980.
2-ethyl-5,6,7-trimethoxy-3-methylquinoline (Q6).
Colorless solid (20mg, 31%). Isolated with 15% ethyl
acetate in hexane. MP: 95-97 C. IR: 3017, 2964,
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-
1 1
2925, 1604, 1484, 1389, 1238, 1093, 1002 cm . H
NMR (500 MHz, CD Cl ) δ 8.04 (s, 1H), 7.17 (s, 1H),
-
1 1
cm . H NMR (500 MHz, CD
2
2
Cl ) δ 8.14 (s, 1H), 7.40
2
2
(
d, J = 8.4 Hz, 2H), 7.24 (s, 1H), 7.20 (d, J = 8.4 Hz,
4.03 (s, 3H), 3.98 (s, 3H), 3.93 (s, 3H), 2.93 (q, J = 7.5
13
1
2
4
H), 7.15 (d, J = 8.4 Hz, 2H), 6.93 (d, J = 8.4 Hz, 2H),
Hz, 2H), 2.46 (s, 3H), 1.33 (t, J = 7.5 Hz, 3H). C{ H}
NMR (125 MHz, CD Cl ) δ 162.2, 155.1, 146.5,
.20 (s, 2H), 4.03 (s, 3H), 4.02 (s, 3H), 3.95 (s, 3H).
2
2
13
1
C{ H} NMR (125 MHz, CD
2
Cl
2
) δ 157.3, 156.4,
144.1, 140.2, 130.0, 127.0, 117.8, 103.4, 61.4, 60.9,
55.9, 28.9, 18.7, 12.3. HRMS (ESI-TOF) m/z:
1
1
6
46.9, 145.1, 140.8, 138.6, 138.3, 133.4, 132.2, 131.6,
31.3, 130.9, 130.2, 128.3, 128.1, 117.6, 103.6, 61.5,
+
+
[(M+H) ] calcd for (C H NO ) 262.1438; Found
1
5
20
3
+
1.0, 56.1, 41.6. HRMS (ESI-TOF) m/z: [(M+H) ]
262.1449.
+
calcd for (C25
H
22Cl
2
NO
3
) 454.0971; Found 454.0986.
3-ethyl-5,6,7-trimethoxy-2-propylquinoline (Q7).
Colorless oil (34mg, 47%). Isolated with 20% ethyl
acetate in hexane. IR: 3010, 2961, 2937, 1601, 1479,
5
,6,7-trimethoxy-2-(4-methoxybenzyl)-3-(4-
methoxyphenyl)quinoline (Q3). Colorless oil (30mg,
7%; ran with 0.1mmol of aromatic amine as 1 equiv).
Isolated with 10% ethyl acetate in hexane. IR: 3062,
-
1 1
6
1373, 1236, 1094, 1001 cm . H NMR (500 MHz,
CD Cl ) δ 8.05 (s, 1H), 7.14 (s, 1H), 4.04 (s, 3H), 3.98
2
2
-1
3
031, 2933, 1611, 1510, 1371, 1210, 1101, 1033 cm .
(s, 3H), 3.92 (s, 3H), 2.91 – 2.87 (m, 2H), 2.82 (q, J =
7.5 Hz, 2H), 1.81 (dd, J = 15.5, 7.5 Hz, 2H), 1.32 (t, J
1
H NMR (500 MHz, CD
2 2
Cl ) δ 8.16 – 8.11 (m, 1H),
13
1
7
6
3
.24 (s, 1H), 7.23 – 7.20 (m, 2H), 6.99 – 6.89 (m, 4H),
= 7.5 Hz, 3H), 1.05 (t, J = 7.5 Hz, 3H). C{ H} NMR
(125 MHz, CD Cl ) δ 161.0, 155.1, 146.6, 144.1,
.75 – 6.69 (m, 2H), 4.20 (s, 2H), 4.03 (s, 3H), 4.02 (s,
2
2
H), 3.95 (s, 3H), 3.87 (s, 3H), 3.74 (s, 3H). 13C{ H}
1
140.1, 133.1, 128.1, 117.8, 103.5, 61.4, 60.9, 55.9,
37.4, 25.2, 22.6, 14.6, 14.1. HRMS (ESI-TOF) m/z:
2 2
NMR (125 MHz, CD Cl ) δ 159.1, 158.7, 157.8,
+
+
156.0, 146.9, 144.9, 140.6, 133.2, 132.5, 132.1, 131.1,
130.7, 129.7, 117.6, 113.5, 113.4, 103.6, 61.5, 61.0,
56.0, 55.3, 55.1, 41.2. HRMS (ESI-TOF) m/z:
[(M+H) ] calcd for (C27
446.1973.
17 24 3
[(M+H) ] calcd for (C H NO ) 290.1751; Found
290.1758.
3-(but-3-en-1-yl)-5,6,7-trimethoxy-2-(pent-4-en-
1-yl)quinoline (Q8). Colorless oil (32mg, 37%).
Isolated with 12% ethyl acetate in hexane. IR: 3074.
+
+
H
28NO
5
) 446.1962; Found
-
1 1
5
,6,7-trimethoxy-2-(4-methylbenzyl)-3-(p-
3001, 2934, 1616, 1566, 1481, 1243, 1093 cm . H
NMR (500 MHz, CD Cl ) δ 8.05 (s, 1H), 7.15 (s, 1H),
tolyl)quinoline (Q4). Colorless oil (27mg, 66%; ran
with 0.1mmol of aromatic amine as 1 equiv). Isolated
with 7.5% ethyl acetate in hexane. IR: 3051, 3019,
2
2
6.04 – 5.85 (m, 2H), 5.18 – 4.98 (m, 4H), 4.04 (s, 3H),
3.99 (s, 3H), 3.94 (s, 3H), 2.95 – 2.86 (m, 4H), 2.48 –
2.43 (m, 2H), 2.23 (q, J = 7.3 Hz, 2H), 1.90 (dt, J =
15.4, 7.6 Hz, 2H). 13C{ H} NMR (125 MHz, CD Cl )
-
1
1
2
935, 1616, 1480, 1370, 1101 cm . H NMR (500
MHz, CD Cl ) δ 8.17 (s, 1H), 7.27 – 7.21 (m, 5H), 7.01
d, J = 8.0 Hz, 2H), 6.91 (d, J = 8.0 Hz, 2H), 4.23 (s,
1
2
2
2
2
(
δ 160.8, 155.2, 146.5, 144.3, 140.2, 138.7, 137.9,
130.7, 129.2, 117.6, 115.0, 114.5, 103.5, 61.4, 61.0,
55.9, 34.7, 34.6, 33.8, 31.7, 28.5. HRMS (ESI-TOF)
2
3
H), 4.04 (s, 3H), 4.03 (s, 3H), 3.96 (s, 3H), 2.44 (s,
1
3
1
2 2
H), 2.28 (s, 3H). C{ H} NMR (125 MHz, CD Cl )
+
+
δ 158.4, 156.0, 146.9, 145.0, 140.7, 137.3, 137.2,
1
1
21 28 3
m/z: [(M+H) ] calcd for (C H NO ) 342.2064;
37.1, 135.3, 133.5, 131.1, 129.5, 128.8, 128.7, 128.6,
17.6, 103.6, 61.5, 61.0, 56.0, 41.5, 20.9, 20.7.HRMS
Found 342.2066.
2-benzyl-5,7-dimethoxy-3-phenylquinoline (Q9).
Yellow solid (68mg, 76%). Isolated with 6.5% ethyl
acetate in hexane. MP: 80-82 C. IR: 3059, 3019,
+
+
(
4
ESI-TOF) m/z: [(M+H) ] calcd for (C27
14.2064; Found 414.2074.
-(3-chlorobenzyl)-3-(3-chlorophenyl)-5,6,7-
3
H28NO )
-1
2
2920, 1628, 1575, 1493, 1382, 1204, 1117, 1044 cm .
1
trimethoxyquinoline (Q5). Colorless oil (82mg, 72%).
Isolated with 7.5% ethyl acetate in hexane. IR: 3059,
2 2
H NMR (500 MHz, CD Cl ) δ 8.27 (s, 1H), 7.44 –
7
7
.37 (m, 3H), 7.32 – 7.29 (m, 2H), 7.21 – 7.15 (m, 2H),
.13 (dd, J = 8.4, 6.0 Hz, 1H), 7.08 – 6.95 (m, 3H),
-
1 1
2
936, 1615, 1475, 1369, 1104, 1037, 783, 683 cm . H
NMR (500 MHz, CD Cl ) δ 8.17 (s, 1H), 7.42 – 7.35
m, 2H), 7.26 (s, 1H), 7.23 (t, J = 1.8 Hz, 1H), 7.18 –
2
2
6.54 (d, J = 2.1 Hz, 1H), 4.28 (s, 2H), 3.97 (s, 3H),
13
1
(
2 2
3.96 (s, 3H). C{ H} NMR (125 MHz, CD Cl ) δ
7.11 (m, 3H), 6.98 (s, 1H), 6.90 – 6.86 (m, 1H), 4.22
161.4, 159.3, 156.1, 149.4, 140.2, 140.0, 132.9, 131.5,
(s, 2H), 4.05 (s, 3H), 4.04 (s, 3H). 3.96 (s, 3H).
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29.6, 128.8, 128.1, 128.0, 127.2, 125.8, 115.0, 99.2,
7.8, 55.8, 55.6, 42.2. HRMS (ESI-TOF) m/z:
13
1
2 2
C{ H} NMR (125 MHz, CD Cl ) δ 156.9, 156.5,
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