G
H. Naruto, H. Togo
Paper
Synthesis
1H NMR (400 MHz, CDCl3): = 7.50 (d, J = 8.5 Hz, 2 H), 7.54 (t, J = 8.1
Hz, 1 H), 7.74 (t, J = 7.7 Hz, 1 H), 7.84 (d, J = 7.9 Hz, 1 H), 7.85 (d, J = 8.6
Hz, 1 H), 8.12–8.17 (m, 3 H), 8.24 (d, J = 8.6 Hz, 1 H).
13C NMR (100 MHz, CDCl3): = 118.5, 126.5, 127.2, 127.5, 128.8,
129.0, 129.7, 129.8, 135.5, 136.9, 138.0, 148.2, 156.0.
2-(p-Biphenyl)quinoline (3N)
Yield: 412.5 mg (73%); white solid; mp 173–174 °C.
IR (neat): 3053, 3035, 1595, 1569 cm–1
1H NMR (400 MHz, CDCl3): = 7.31 (td, J = 7.4, 2.0 Hz, 1 H), 7.49 (t, J =
7.9 Hz, 2 H), 7.54 (td, J = 7.6, 1.1 Hz, 1 H), 7.69 (d, J = 7.0 Hz, 2 H), 7.75
(td, J = 7.7, 1.4 Hz, 1 H), 7.78 (d, J = 8.6 Hz, 2 H), 7.85 (d, J = 8.2 Hz, 1 H),
7.94 (d, J = 8.6 Hz, 1 H), 8.19 (d, J = 8.4 Hz, 1 H), 8.24–8.28 (m, 3 H).
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HRMS (ESI): m/z [M + H]+ calcd for C15H11NCl: 240.0575; found:
240.0573.
13C NMR (100 MHz, CDCl3): = 118.8, 126.3, 127.1, 127.2, 127.4,
127.5, 127.6, 127.9, 128.8, 129.7 (2 C), 136.8, 138.5, 140.5, 142.0,
148.3, 156.8.
2-(3-Bromophenyl)quinoline (3J)
Yield: 370.5 mg (65%); white solid; mp 66–67 °C.
IR (neat): 3061, 2987, 1594, 1550 cm–1
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HRMS (ESI): m/z [M + H]+ calcd for C21H16N: 282.1277; found:
1H NMR (400 MHz, CDCl3): = 7.40 (t, J = 7.9 Hz, 1 H), 7.55 (t, J = 7.0
Hz, 1 H), 7.59 (d, J = 8.8 Hz, 1 H), 7.75 (t, J = 7.0 Hz, 1 H), 7.84 (d, J = 8.4
Hz, 1 H), 7.85 (d, J = 8.5 Hz, 1 H), 8.08 (d, J = 7.7 Hz, 1 H), 8.17 (d, J = 8.6
Hz, 1 H), 8.25 (d, J = 8.6 Hz, 1 H), 8.35–8.36 (m, 1 H).
13C NMR (100 MHz, CDCl3): = 118.6, 123.1, 126.0, 126.6, 127.3,
127.4, 129.7, 129.8, 130.3, 130.6, 132.1, 136.9, 141.6, 148.1, 155.5.
282.1272.
2-(4-Phenoxyphenyl)quinoline (3O)
Yield: 507.3 mg (85%); white solid; mp 116–117 °C.
IR (neat): 3063, 3038, 1589 cm–1
1H NMR (400 MHz, CDCl3): = 7.08 (dd, J = 8.6, 0.9 Hz, 2 H), 7.14–7.17
(m, 3 H), 7.38 (t, J = 7.9 Hz, 2 H), 7.52 (td, J = 7.6, 1.1 Hz, 1 H), 7.72 (td,
J = 7.7, 1.4 Hz, 1 H), 7.81–7.86 (m, 2 H), 8.14–8.17 (m, 3 H), 8.21 (d, J =
8.6 Hz, 1 H).
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HRMS (ESI): m/z [M + H]+ calcd for C15H11N79Br: 284.0069; found:
284.0070.
2-(4-Bromophenyl)quinoline (3K)
13C NMR (100 MHz, CDCl3): = 118.7, 118.9, 119.2, 123.6, 126.1,
127.0, 127.4, 129.1, 129.6, 129.7, 129.8, 134.7, 136.8, 148.3, 156.7,
156.8, 158.6.
HRMS (ESI): m/z [M + H]+ calcd for C21H16ON: 298.1226; found:
298.1223.
Yield: 342.7 mg (60%); white solid; mp 109–110 °C.
IR (neat): 3057, 3034, 1594, 1550 cm–1
1H NMR (400 MHz, CDCl3): = 7.54 (td, J = 7.6, 1.1 Hz, 1 H), 7.66 (d, J =
8.6 Hz, 2 H), 7.74 (td, J = 7.8, 1.6 Hz, 1 H), 7.84 (d, J = 8.2 Hz, 1 H), 7.85
(d, J = 8.6 Hz, 1 H), 8.06 (d, J = 8.6 Hz, 2 H), 8.16 (d, J = 8.6 Hz, 1 H), 8.24
(d, J = 8.6 Hz, 1 H).
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2-(1,3-Benzodioxol-5-yl)quinoline (3P)
13C NMR (100 MHz, CDCl3): = 118.5, 123.9, 126.5, 127.2, 127.5,
Yield: 299.6 mg (60%); white solid; mp 85–86 °C.
IR (neat): 2992, 2900, 1595, 1486, 1247, 1037 cm–1
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129.1, 129.7, 129.8, 131.9, 136.9, 138.5, 148.2, 156.0.
HRMS (ESI): m/z [M + H]+ calcd for C15H11N79Br: 284.0069; found:
284.0067.
1H NMR (400 MHz, CDCl3): = 6.05 (s, 2 H), 6.95 (d, J = 8.2 Hz, 1 H),
7.51 (td, J = 7.6, 1.1 Hz, 1 H), 7.66 (dd, J = 8.2, 1.6 Hz, 1 H), 7.69–7.75
(m, 2 H), 7.79–7.82 (m, 2 H), 8.13 (d, J = 8.6 Hz, 1 H), 8.18 (d, J = 8.6 Hz,
1 H).
2-[4-(Trifluoromethyl)phenyl]quinoline (3L)
13C NMR (100 MHz, CDCl3): = 101.3, 107.9, 108.5, 118.6, 121.7,
126.0, 127.0, 127.4, 129.5, 129.6, 134.1, 136.7, 148.1, 148.4, 148.8,
156.6.
HRMS (ESI): m/z [M + H]+ calcd for C16H12O2N: 250.0863; found:
250.0860.
Yield: 318.6 mg (58%); white solid; mp 121–122 °C.
IR (neat): 3073, 2983, 1594, 1556 cm–1
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1H NMR (400 MHz, CDCl3): = 7.58 (t, J = 7.9 Hz, 1 H), 7.75–7.80 (m,
3 H), 7.86 (d, J = 8.2 Hz, 1 H), 7.90 (d, J = 8.6 Hz, 1 H), 8.19 (d, J = 8.4 Hz,
1 H), 8.27–8.30 (m, 3 H).
13C NMR (100 MHz, CDCl3): = 118.7, 124.2 (q, JC-F = 272.5 Hz), 125.7
2-[4-(Methoxymethoxy)phenyl]quinoline (3Q)
(d, JC-F = 3.8 Hz), 126.8, 127.4, 127.5, 127.7, 129.8, 129.9, 131.0 (q, JC-F
=
Yield: 415.5 mg (78%); white solid; mp 64–65 °C.
32.0 Hz), 137.6, 142.8, 148.2, 155.5.
IR (neat): 2988, 1595, 1495, 1249 cm–1
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HRMS (ESI): m/z [M + H]+ calcd for C16H11NF3: 274.0838; found:
1H NMR (400 MHz, CDCl3): = 3.52 (s, 3 H), 5.26 (s, 2 H), 7.19 (d, J =
8.8 Hz, 2 H), 7.51 (t, J = 6.8 Hz, 1 H), 7.71 (t, J = 7.0 Hz, 1 H), 7.80–7.85
(m, 2 H), 8.12–8.15 (m, 3 H), 8.19 (d, J = 8.6 Hz, 1 H).
274.0835.
2-(-Naphthyl)quinoline (3M)
13C NMR (100 MHz, CDCl3): = 56.1, 94.3, 116.4, 118.6, 126.0 (2 C),
Yield: 374.3 mg (73%); yellow solid; mp 145–147 °C.
IR (neat): 3053, 2925, 1594, 1556 cm–1
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126.9, 127.4, 128.8, 129.6, 133.4, 136.6, 148.2, 156.8, 158.3.
HRMS (ESI): m/z [M + H]+ calcd for C17H16O2N: 266.1176; found:
266.1171.
1H NMR (400 MHz, CDCl3): = 7.52–7.57 (m, 3 H), 7.76 (td, J = 7.7, 1.4
Hz, 1 H), 7.86 (d, J = 8.0 Hz, 1 H), 7.88–7.92 (m, 1 H), 7.99–8.02 (m,
2 H), 8.05 (d, J = 8.6 Hz, 1 H), 8.23 (d, J = 8.4 Hz, 1 H), 8.27 (d, J = 8.6 Hz,
1 H), 8.38 (dd, J = 8.7, 1.7 Hz, 1 H), 8.62 (s, 1 H).
7-Methyl-2-phenylquinoline (3R)
13C NMR (100 MHz, CDCl3): = 119.1, 125.0, 126.3, 126.7, 127.1, 127.2
(2 C), 127.5, 127.7, 128.4, 128.6, 128.8, 129.7, 133.5, 133.8, 136.8,
136.9, 148.3, 157.1.
Yield: 321.5 mg (73%); white solid; mp 61–62 °C.
IR (neat): 2987, 2901, 1596, 1550 cm–1
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HRMS (ESI): m/z [M + H]+ calcd for C19H14N: 256.1121; found:
256.1118.
© 2020. Thieme. All rights reserved. Synthesis 2020, 52, A–I