The Journal of Organic Chemistry
Page 10 of 18
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2-(2,4-dinitrobenzyl)-6-nitroquinoline (3e). 12 h, 36.8 mg, 52% yield, brown solid; mp:
178-180 °C; 1H NMR (500 MHz, CDCl3) δ 8.92 (d, J = 2.1 Hz, 1H), 8.75 (d, J = 2.2 Hz, 1H), 8.46
(dd, J = 8.4, 2.2 Hz, 1H), 8.41 (dd, J = 9.3, 2.3 Hz, 1H), 8.32 (d, J = 8.5 Hz, 1H), 7.97 (d, J = 9.2
Hz, 1H), 7.76 (d, J = 8.4 Hz, 1H), 7.57 (d, J = 8.5 Hz, 1H), 4.87 (s, 2H) ppm; 13C NMR (125 MHz,
CDCl3) δ 161.1, 149.8, 147.3, 145.6, 139.7, 138.8, 134.8, 131.0, 127.3, 125.8, 124.4, 123.4, 123.3,
120.6, 42.4 ppm. HRMS (ESI): calcd for C16H11N4O6 [M+H]+ : 355.0679, found 355.0682.
2-(2,4-dinitrobenzyl)-7-fluoroquinoline (3f). 14 h, 37.9 mg, 58% yield, brown solid; mp:
100-103 °C; 1H NMR (500 MHz, DMSO) δ 8.76 (s, 1H), 8.50 (d, J = 8.3 Hz, 1H), 8.34 (d, J = 8.2
Hz, 1H), 7.99 (dd, J = 16.9, 9.8 Hz, 1H), 7.88 (d, J = 8.3 Hz, 1H), 7.51 – 7.37 (m, 3H), 4.81 (s, 2H)
ppm; 13C NMR (125 MHz, DMSO) δ 163.4, 161.5, 159.2, 149.4, 147.8, 147.7, 146.4, 140.0, 136.9,
134.8, 130.5, 130.4, 127.3, 123.7, 121.0, 119.8, 116.4, 116.2, 111.8, 111.6, 40.9 ppm. HRMS
(ESI): calcd for C16H11FN3O4 [M+H]+ : 328.0734, found 328.0740.
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7-chloro-2-(2,4-dinitrobenzyl)quinoline (3g). 15 h, 35.7 mg, 52% yield, brown solid; mp:
130-133 °C; 1H NMR (500 MHz, DMSO) δ 8.77 (s, 1H), 8.52 (d, J = 8.1 Hz, 1H), 8.36 (d, J = 8.2
Hz, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.90 (d, J = 8.4 Hz, 1H), 7.72 (s, 1H), 7.55 (t, J = 10.0 Hz, 2H),
4.84 (s, 2H) ppm; 13C NMR (125 MHz, DMSO) δ 159.3, 149.4, 147.1, 146.5, 139.9, 136.9, 134.8,
134.2, 129.8, 127.4, 126.9, 126.8, 125.1, 122.0, 119.9, 40.9 ppm. HRMS (ESI): calcd for
C16H11ClN3O4 [M+H]+ : 344.0438, found 344.0440.
2-((2,4-dinitrophenyl)(phenylsulfonyl)methyl)quinoline (3h). 12 h, 73.6 mg, 82% yield, brown
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solid; mp: 171-173 °C; H NMR (500 MHz, CDCl3) δ 9.21 – 9.18 (m, 1H), 8.67 (d, J = 2.4 Hz,
1H), 8.53 (dd, J = 8.8, 2.4 Hz, 1H), 8.16 (d, J = 8.4 Hz, 1H), 8.08 (d, J = 8.5 Hz, 1H), 7.83 (t, J =
6.7 Hz, 1H), 7.76 (ddd, J = 8.4, 6.9, 1.4 Hz, 1H), 7.61 (qd, J = 8.3, 1.1 Hz, 4H), 7.50 (d, J = 8.4
Hz, 1H), 7.45 – 7.41 (m, 2H), 6.80 (s, 1H) ppm; 13C NMR (125 MHz, CDCl3) δ 150.3, 149.9,
147.9, 147.7, 137.5, 137.3, 135.9, 134.7, 132.4, 130.4, 129.9, 129.4, 129.3, 127.9, 127.7, 127.6,
126.3, 123.5, 119.9, 69.7 ppm. HRMS (ESI): calcd for C22H16N3O6S [M+H]+ : 450.0760, found
450.0764.
7-chloro-2-((2,4-dinitrophenyl)(phenylsulfonyl)methyl)quinoline (3i). 12 h, 71.5 mg, 74% yield,
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brown solid; mp: 207-210 °C; H NMR (500 MHz, DMSO) δ 9.02 – 8.97 (m, 1H), 8.67 (dd, J =
7.3, 2.3 Hz, 2H), 8.49 (d, J = 8.5 Hz, 1H), 8.07 (dd, J = 15.0, 5.3 Hz, 2H), 7.74 – 7.71 (m, 2H),
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