Page 13 of 21
The Journal of Organic Chemistry
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(2-Chlorophenyl)(quinolin-8-yl)methanone (3an) White solid, m.p. 95-98 °C, yield 42% (22.4
mg), Rf = 0.30 (hexanes/EtOAc 15:1 (v/v)). NMR Spectroscopy: 1H NMR (400 MHz, CDCl3) δ
8.79 (dd, J = 4.4, 2.0 Hz, 1H), 8.18 (dd, J = 8.4, 1.6 Hz, 1H), 7.98 (dd, J = 8.4, 1.6 Hz, 1H), 7.92
(dd, J = 7.2, 1.2 Hz, 1H), 7.62 (ddd, J = 12.0, 6.4, 4.4 Hz, 2H), 7.42 – 7.36 (m, 3H), 7.33 – 7.30
(m, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 196.9, 151.0, 146.2, 139.7, 138.9, 136.1, 132.6,
132.0, 131.7, 131.2, 130.6, 128.3, 126.7, 126.1, 121.7. Mass Spectrometry: HRMS - ESI (m/z)
calcd for C16H11ClNO [M+H]+ 268.0524 found, 268.0528. The compound is new compound.
(3-Chlorophenyl)(quinolin-8-yl)methanone (3ao) White solid, m.p. 96-98 °C, yield 75% (40.0
mg), Rf = 0.30 (hexanes/EtOAc 15:1 (v/v)), NMR Spectroscopy: 1H NMR (400 MHz, CDCl3) δ
8.82 (dd, J = 4.0, 1.6 Hz, 1H), 8.22 (dd, J = 8.4, 1.6 Hz, 1H), 7.98 (dd, J = 8.4, 1.2 Hz, 1H), 7.82
(t, J = 1.6 Hz, 1H), 7.74 (dd, J = 6.8, 1.2 Hz, 1H), 7.64 (dd, J = 14.8, 6.8 Hz, 2H), 7.52 – 7.50 (m,
1H), 7.42 (dd, J = 8.4, 4.4 Hz, 1H), 7.33 (t, J = 8.0 Hz, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ
196.8, 151.0, 146.1, 139.8, 138.6, 136.2, 134.7, 133.2, 130.3, 130.0, 129.8, 128.6, 128.5, 128.3,
126.1, 121.9. Mass Spectrometry: HRMS - ESI (m/z) calcd for C16H11ClNO [M+H]+ 268.0524
found, 268.0530. The compound is new compound.
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2-(Quinoline-8-carbonyl)benzaldehyde (3ap) White solid, m.p. 133-135 °C, yield 69% (36.1 mg),
Rf = 0.05 (hexanes/EtOAc 15:1 (v/v)), NMR Spectroscopy: 1H NMR (400 MHz, CDCl3) δ 10.50
(s, 1H), 8.73 (dd, J = 4.0, 1.6 Hz, 1H), 8.20 (dd, J = 8.4, 1.6 Hz, 1H), 8.01 (d, J = 8.0 Hz, 2H),
7.94 (dd, J = 6.8, 1.2 Hz, 1H), 7.65 (dd, J = 8.0, 7.6 Hz, 1H), 7.59 (t, J = 7.6 Hz, 1H), 7.45 (td, J =
7.6, 1.2 Hz, 1H), 7.39 (dd, J = 8.4, 4.4 Hz, 1H), 7.34 (dd, J = 7.6, 0.4 Hz, 1H). 13C{1H} NMR
(100 MHz, CDCl3) δ 198.9, 192.5, 151.0, 146.1, 142.6, 138.3, 136.6, 136.2, 132.5, 131.7, 130.6,
130.3, 128.41, 128.37, 126.1, 121.8. Mass Spectrometry: HRMS - ESI (m/z) calcd for
C17H12NO2 [M+H]+ 262.0863 found, 262.0868. The compound is new compound.
(3-Nitrophenyl)(quinolin-8-yl)methanone (3aq) White solid, m.p. 145-146 °C, yield 75% (42.0
mg), Rf = 0.10 (hexanes/EtOAc 15:1 (v/v)). NMR Spectroscopy: 1H NMR (400 MHz, CDCl3) δ
8.76 (d, J = 2.8 Hz, 1H), 8.56 (s, 1H), 8.39 (d, J = 7.6 Hz, 1H), 8.25 (d, J = 8.0 Hz, 1H), 8.14 (d, J
= 7.6 Hz, 1H), 8.04 (d, J = 8.0 Hz, 1H), 7.83 (d, J = 7.2 Hz, 1H), 7.68 (t, J = 7.6 Hz, 1H), 7.61 (t,
J = 7.6 Hz, 1H), 7.44 (dd, J = 8.4, 4.4 Hz, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 196.0, 151.0,
148.4, 146.0, 139.6, 137.8, 136.4, 135.5, 131.0, 129.6, 129.3, 128.4, 127.4, 126.3, 124.9, 122.1.
Mass Spectrometry: HRMS - ESI (m/z) calcd for C16H11N2O3 [M+H]+ 279.0764 found,
279.0770. The compound is new compound.
(3,4-di-Chlorophenyl)(quinolin-8-yl)methanone (3ar) White solid, m.p. 138-139 °C, yield 70%
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(42.4 mg), Rf = 0.50 (hexanes/EtOAc 10:1 (v/v)). NMR Spectroscopy: H NMR (400 MHz,
CDCl3) δ 8.82 (dd, J = 4.0, 1.6 Hz, 1H), 8.23 (dd, J = 8.4, 2.0 Hz, 1H), 8.00 (dd, J = 8.4, 1.6 Hz,
1H), 7.90 (d, J = 2.0 Hz, 1H), 7.76 (dd, J = 7.2, 1.6 Hz, 1H), 7.65 (dd, J = 8.4, 7.6 Hz, 1H), 7.60
(dd, J = 8.4, 2.0 Hz, 1H), 7.47 (d, J = 8.4 Hz, 1H), 7.44 (dd, J = 8.4, 4.4 Hz, 1H). 13C{1H} NMR
(100 MHz, CDCl3) δ 195.9, 151.0, 146.0, 138.2, 137.7, 137.6, 136.2, 133.0, 131.8, 130.5, 130.4,
129.2, 128.7, 128.2, 126.1, 121.9. Mass Spectrometry: HRMS - ESI (m/z) calcd for
C16H10Cl2NO [M+H]+ 302.0134 found, 302.0140. The compound is new compound.
(3,5-di-Fluorophenyl)(quinolin-8-yl)methanone (3as) White solid, m.p. 122-124 °C, yield 83%
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(44.5 mg), Rf = 0.55 (hexanes/EtOAc 10:1 (v/v)). NMR Spectroscopy: H NMR (400 MHz,
CDCl3) δ 8.82 (dd, J = 4.0, 1.6 Hz, 1H), 8.23 (dd, J = 8.4, 2.0 Hz, 1H), 8.00 (dd, J = 8.4, 1.2 Hz,
1H), 7.76 (dd, J = 6.8, 1.2 Hz, 1H), 7.65 (dd, J = 8.0, 7.2 Hz, 1H), 7.44 (dd, J = 8.0, 4.0 Hz, 1H),
7.34 – 7.28 (m, 2H), 7.00 (tt, J = 8.4, 2.4 Hz, 1H). 13C{1H} NMR (100 MHz, CDCl3) δ 195.7 (t, J
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