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The Journal of Organic Chemistry
(d, J = 9.0 Hz, 2H), 7.03 (br, s, 1H, NH), 6.96-6.97 (m, 2H), 6.94
νmax (cm-1): 3354, 2320, 1604, 1570, 1544, 1330, 1234, 1114,
1031, 966, 891, 763. HRMS (ESI-TOF) (m/z): [M+H]+ calcd for
C17H13ClF3N2O, 353.0663; found, 353.0688.
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(d, J = 9.0 Hz, 1H), 3.85 (s, 3H). 13C{1H} NMR (150 MHz,
CDCl3, δ): 157.7, 157.4, 151.6, 142.6, 139.0, 131.6, 127.4, 124.8,
124.5, 123.9, 122.5, 114.9, 112.9, 55.7. IR (ZnSe) νmax (cm-1):
2922, 2845, 1735, 1624, 1575, 1462, 1325, 1278, 1226, 948, 837,
792. HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C16H14N3O3,
296.1030; found, 296.1045.
N-(4-methoxyphenyl) benzo[f]quinolin-3-amine (Table 2, entry
3oa). Off white solid, yield = 41.4 mg (46%). mp 174-175 °C.
Isolated from flash chromatography (10% EtOAc/n-hexane). 1H
NMR (600 MHz, DMSO-d6, δ): 9.30 (s, br, NH, 1H), 8.89 (d, J =
9.0 Hz, 1H), 8.60 (d, J = 8.4 Hz, 1H), 7.94-7.98 (m, 2H), 7.86 (d,
J = 9.0 Hz, 2H), 7.68 (d, J = 9.0 Hz, 1H), 7.64-7.66 (m, 1H), 7.52-
7.55 (m, 1H), 7.12 (d, J = 9.0 Hz, 1H), 6.94 (d, J = 9.0 Hz, 2H),
3.75 (s, 3H). 13C{1H} NMR (150 MHz, DMSO-d6, δ): 154.9,
153.9, 146.7, 134.7, 132.3, 130.3, 129.9, 129.6, 128.4, 126.9,
126.8, 125.2, 121.9, 120.1, 118.2, 113.9, 112.4, 55.2. IR (ZnSe):
νmax (cm-1) 3410, 2536, 1597, 1506, 1473, 1394, 1246, 1174,
1029, 819, 761. HRMS (ESI-TOF) (m/z): [M+H]+ calcd for
C20H17N2O, 301.1335; found, 301.1355.
Isoquinolin-1-yl-(4-methoxy-phenyl)-amine (Table 2, entry 3pa).
Red-brown solid, yield = 26.3 mg (35%). mp 123-124 °C. Isolat-
ed from flash chromatography (10% EtOAc/n-hexane). 1H NMR
(300 MHz, CDCl3, δ): 8.05 (d, J = 5.7 Hz, 1H), 7.90 (d, J = 8.1
Hz, 1H), 7.73 (d, J = 8.1 Hz, 1H), 7.60-7.65 (m, 1H), 7.49 – 7.54
(m, 3H), 7.07 (d, J = 5.7 Hz, 1H), 6.91-6.95 (m, 2H), 3.81 (s, 3H).
13C{1H} NMR (75 MHz, CDCl3, δ): 155.9, 153.2, 141.2, 137.6,
133.7, 129.9, 127.5, 126.4, 123.2, 121.6, 118.7, 114.5, 112.9,
55.7. IR (ZnSe): νmax (cm-1) 3695, 3664, 3421, 2964, 1562, 1477,
1388, 1247, 1055, 960, 864, 796. HRMS (ESI-TOF) (m/z):
[M+H]+ calcd for C16H15N2O, 251.1179; found, 251.1175.
2-(4-Methoxy-phenylamino)-quinoline-6-carboxylic acid methyl
ester (Table 2, entry 3ja). Brown solid, yield = 40.1 mg (35%).
mp 125-126 °C. Isolated from flash chromatography (20%
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EtOAc/n-hexane). H NMR (600 MHz, CDCl3, δ): 8.37 (s, 1H),
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8.15 (dd, J = 8.4, 1.2 Hz, 1H), 7.92 (d, J = 9.0 Hz, 1H), 7.69 (d, J
= 9.0 Hz, 1H), 7.43 (d, J = 9.0 Hz, 2H), 6.94 (d, J = 9.0 Hz, 2H),
6.88 (d, J = 9.0 Hz, 1H), 3.95 (s, 3H), 3.83 (s, 3H). 13C{1H} NMR
(150 MHz, CDCl3, δ): 167.2, 157.1, 150.8, 138.8, 132.4, 130.7,
129.9, 126.6, 124.6, 124.3, 123.2, 116.5, 114.9, 111.8, 55.7, 52.2.
IR (ZnSe) νmax (cm-1): 3363, 2837, 1710, 1620, 1537, 1508, 1242,
1128, 1033, 962, 756. HRMS (ESI-TOF) (m/z): [M+H]+ calcd for
C18H17N2O3, 309.1234; found, 309.1231.
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6-Isopropyl-N-(4-methoxyphenyl) quinolin-2-amine (Table 2,
entry 3ka). Yellow viscous compound, yield = 40.3 mg (46%).
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Isolated from flash chromatography (10% EtOAc/n-hexane). H
NMR (600 MHz, CDCl3, δ): 7.83 (d, J = 9.0 Hz, 1H), 7.68 (d, J =
9.0 Hz, 1H), 7.48 (dd, J = 8.4, 1.8 Hz, 1H), 7.43 (d, J = 2.4 Hz,
1H), 7.39-7.41 (m, 2H), 6.91 (d, J = 9.0 Hz, 2H), 6.86 (d, J = 9.0
Hz, 1H), 3.82 (s, 3H), 3.00-3.06 (m, 1H), 1.32 (d, J = 7.2 Hz, 6H).
13C{1H} NMR (150 MHz, CDCl3, δ): 156.4, 155.1, 146.4, 143.4,
137.7, 133.3, 129.6, 126.3, 123.98, 123.94, 114.7, 110.9, 55.7,
33.9, 24.2. IR (ZnSe): νmax (cm-1) 3392, 2958, 1604, 1494, 1398,
1230, 1178, 1033, 885, 829, 734. HRMS (ESI-TOF) (m/z):
[M+H]+ calcd for C19H21N2O, 293.1648; found, 293.1640.
(4-Methoxy-phenyl)-(5-nitro-quinolin-2-yl)-amine (Table 2,
entry 3la). Yellow solid, yield = 46.0 mg (52%). mp 135-136 °C.
Isolated from flash chromatography (15% EtOAc/n-hexane). 1H
NMR (600 MHz, CDCl3, δ): 8.62 (d, J = 9.6 Hz, 1H), 7.98 (d, J =
7.8 Hz, 1H), 7.93 (d, J = 8.4 Hz, 1H), 7.54 (t, J = 7.8 Hz, 1H),
7.44 (d, J = 8.4 Hz, 2H), 7.23 (br, s, 1H, NH), 7.01 (d, J = 9.6 Hz,
1H), 6.93 (d, J = 8.4 Hz, 2H), 3.82 (s, 3H). 13C{1H} NMR (150
MHz, CDCl3, δ): 156.9, 155.8, 148.6, 145.9, 133.2, 133.1, 132.1,
127.9, 124.2, 120.3, 116.6, 114.7, 114.3, 55.7. IR (ZnSe) νmax (cm-
1): 2972, 2326, 1710, 1508, 1217, 1186, 1033, 954, 871, 790;
HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C16H14N3O3,
296.1030; found, 296.1048.
2-(4-Methoxy-phenylamino)-quinolin-8-ol (Table 2, entry 3ma).
Brown solid, yield = 25.5 mg (32%). mp 141-142 °C. Isolated
from flash chromatography (20% EtOAc/n-hexane). 1H NMR
(600 MHz, CDCl3, δ): 7.88 (d, J = 9.0 Hz, 1H), 7.38 (dd, J = 6.6,
J = 2.4 Hz, 2H), 7.15 – 7.19 (m, 2H), 7.08- 7.09 (m, 1H), 6.93 –
6.96 (m, 2H), 6.84 (d, J = 9.0 Hz, 1H), 6.58 (br, s, 1H, NH), 3.84
(s, 3H). 13C{1H} NMR (150 MHz, CDCl3, δ): 156.7, 154.0,
150.3, 138.0, 137.1, 132.6, 124.1, 123.9, 123.5, 117.9, 114.7,
112.0, 110.7, 55.7. IR (ZnSe): νmax (cm-1) 3697, 3354, 2949, 2864,
1602, 1521, 1438, 1344, 1232, 1033, 956, 756. HRMS (ESI-TOF)
(m/z): [M+H]+ calcd for C16H15N2O2, 267.1128; found, 267.1137.
(4-Chloro-7-trifluoromethyl-quinolin-2-yl)-4-
methoxyphenylamine (Table 2, entry 3na). Pale yellow solid, yield
= 55.0 mg (52%). mp 191-192°C. Isolated from flash chromatog-
raphy (15% EtOAc/n-hexane). 1H NMR (600 MHz, CDCl3, δ):
8.16 (d, J = 8.4 Hz, 1H), 8.11 (s, 1H), 7.66 (d, J = 7.8 Hz, 1H),
7.28 (d, J = 7.2 Hz, 2H), 7.11 (s, 1H), 6.97 (d, J = 6.0 Hz, 2H),
3.84 (s, 3H). 13C{1H} NMR (150 MHz, CDCl3, δ): δ 159.4, 154.1,
148.4, 138.8, 135.3 (q, J = 34.5 Hz, 1C), 127.5, 126.7, 126.6,
125.7, 122.3, 121.69, 121.67, 123.02 (q, J = 271.5 Hz, 1C), 118.1,
115.5, 112.5, 55.8. 19F (565 MHz, CDCl3, δ): -63.1. IR (ZnSe)
(4-Methoxy-phenyl)-pyridin-2-yl-amine (Table 2, entry 3qa).20
Red-brown solid, yield = 24.8 mg (33%). mp 80-81 °C. Isolated
from flash chromatography (25% EtOAc/n-hexane). 1H NMR
(600 MHz, CDCl3, δ): 8.14 (d, J = 6.0 Hz, 1H), 7.41-7.44 (m,
1H), 7.23 (dd, J = 6.6, J = 1.8 Hz, 2H), 6.88-6.91 (m, 2H), 6.65-
6.69 (m, 2H), 3.81 (s, 3H). 13C{1H} NMR (150 MHz, CDCl3, δ):
157.5, 156.4, 148.4, 137.8, 133.4, 124.3, 114.8, 114.4, 107.3,
55.7. IR (ZnSe): νmax (cm-1) 3705, 2937, 2845, 1597, 1454, 1330,
1244, 1168, 1033, 989, 812, 754. HRMS (ESI-TOF) (m/z):
[M+H]+ calcd for C12H13N2O, 201.1022; found, 201.1043.
(4-Methoxy-phenyl)-(4-nitro-pyridin-2-yl)-amine (Table 2,
entry 3ra). Red-brown solid, yield: 29.4 mg (40%). mp 128-129
°C. Isolated from flash chromatography (20% EtOAc/n-hexane).
1H NMR (600 MHz, CDCl3, δ): 8.42 (d, J = 5.4 Hz, 1H), 7.40 (d,
J = 4.8 Hz, 1H), 7.37 (s, 1H), 7.34 (d, J = 9.0 Hz, 2H), 7.04 (d, J
= 8.4 Hz, 2H), 3.93 (s, 3H). 13C{1H} NMR (150 MHz, CDCl3, δ):
159.5, 157.6, 155.8, 150.9, 131.5, 125.3, 115.2, 106.4, 99.8, 55.7.
IR (ZnSe): νmax (cm-1) 3705, 2951, 1627, 1543, 1438, 1354, 1240,
1182, 1033, 995, 866, 731. HRMS (ESI-TOF) (m/z): [M+H]+
calcd for C12H12N3O3, 246.0873; found, 246.0870.
[4-(2,5-Dibutoxy-morpholin-4-yl)-phenyl]-quinolin-2-yl-amine
(Table 2, entry 3ab). White solid, yield: 27.0 mg (20%). m.p. 65-
69 °C. Isolated from flash chromatography (10% EtOAc/n-
hexane). 1H NMR (600 MHz, CDCl3, δ): 8.52 (s, 1H), 7.88 (d, J =
9.0 Hz, 1H), 7.75 (d, J = 8.4 Hz, 1H), 7.63 (d, J = 7.2 Hz, 1H),
7.56-7.59 (m, 1H), 7.26-7.29 (m, 1H), 7.13 (br, s, NH, 1H), 6.84
(d, J = 9.0 Hz, 1H), 6.58(s, 1H), 4.13 (t, J = 6.6 Hz, 2H), 4.02 (t, J
= 6.6 Hz, 2H), 3.89 – 3.91 (m, 4H), 3.08-3.09 (m, 4H), 1.86-1.90
(m, 2H), 1.78-1.83 (m, 2H), 1.54-1.59 (m, 2H), 1.48-1.53 (m,
2H), 1.01-1.04 (m, 3H), 0.98-1.00 (m, 3H). 13C{1H} NMR (150
MHz, CDCl3, δ): 154.1, 145.9, 137.3, 135.5, 129.7, 127.5, 126.9,
124.04, 123.03, 113.4, 110.3, 106.4, 104.1, 69.8, 68.6, 67.5, 51.7,
31.78, 31.76, 19.7, 19.5, 14.09, 14.06. IR (ZnSe): νmax (cm-1)
3427, 2924, 2852, 1606, 1514, 1413, 1373, 1195, 1043, 947, 869,
758. HRMS (ESI-TOF) (m/z): [M+H]+ calcd for C27H36N3O3,
450.2751; found, 450.2771.
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