H
C. Praveen, P. T. Perumal
Paper
Synthesis
2-Methoxy-6-(8-methoxy-4-methyl-6-nitroquinolin-2-yl)-4-ni-
trophenylamine (2m)
Anal. Calcd for C22H22N2O4: C, 69.83; H, 5.86; N, 7.40. Found: C, 70.09;
H, 5.79; N, 7.32.
Yield: 230 mg (60%); brown solid; mp 264–266 °C.
3,5-Dimethyl-2-(4,5,7-trimethylquinolin-2-yl)aniline (2q)
IR (KBr): 3369, 2924, 1615, 1501, 1323, 1093, 740 cm–1
.
Yield: 261 mg (90%); pale yellow solid; mp 114–116 °C.
1H NMR (500 MHz, DMSO-d6): δ = 8.71 (s, 1 H), 8.55 (s, 1 H), 7.80 (s, 1
H), 7.67 (s, 2 H), 6.12 (br s, 2 H), 4.07 (s, 3 H), 3.93 (s, 3 H), 2.47 (s, 3
H).
13C NMR (125 MHz, DMSO-d6): δ = 157.1, 153.7, 146.2, 145.9, 145.5,
144.2, 141.9, 135.9, 129.1, 121.0, 119.2, 113.4, 105.5, 101.6, 100.0,
60.3, 57.0, 21.2.
IR (KBr): 3436, 3277, 1513, 1207, 918, 799 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 7.62 (s, 1 H), 7.41 (s, 1 H), 6.97 (s, 1 H),
6.53 (s, 1 H), 6.07 (br s, 2 H), 2.59 (s, 3 H), 2.54 (s, 3 H), 2.37, (s, 3 H),
2.34 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 158.2, 145.7, 143.0, 140.5, 139.2,
138.1, 135.1, 130.1, 128.8, 125.0, 124.4, 123.0, 120.0, 119.9, 118.5,
20.2, 20.1, 19.7, 19.0, 18.9.
MS (ESI): m/z = 385 [M + H+].
Anal. Calcd for C18H16N4O6: C, 56.25; H, 4.20; N, 14.58. Found: C,
56.45; H, 4.12; N, 14.49.
MS (ESI): m/z = 291 [M + H+].
Anal. Calcd for C20H22N2: C, 82.72; H, 7.64; N, 9.65. Found: C, 83.01; H,
7.56; N, 9.45.
Methyl 2-(2-Amino-3-methoxy-5-methoxycarbonylphenyl)-
8-methoxy-4-methylquinoline-6-carboxylate (2n)
Yield: 312 mg (76%); colorless solid; mp 156–158 °C.
2-(4,5-Dimethylquinolin-2-yl)-3-methylaniline (2r)
IR (KBr): 3394, 2955, 1677, 1081, 756 cm–1
.
Yield: 225 mg (86%); pale yellow solid; mp 139–141 °C.
IR (KBr): 3319, 3021, 1525, 1199, 904, 754 cm–1
.
1H NMR (500 MHz, CDCl3): δ = 8.14 (s, 1 H), 8.06 (s, 1 H), 7.41 (s, 1 H),
7.31 (s, 1 H), 7.21 (d, J = 3.05 Hz, 1 H), 6.58 (br s, 2 H), 3.96 (s, 3 H),
3.91 (s, 3 H), 3.89 (s, 3 H), 3.88 (s, 3 H), 2.60 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 168.4, 166.9, 150.1, 146.6, 145.7,
145.3, 131.2, 128.4, 127.1, 125.0, 122.5, 117.3, 116.1, 115.5, 112.9,
104.3, 102.4, 55.9, 55.5, 51.9, 29.7, 28.1.
1H NMR (500 MHz, CDCl3): δ = 7.88 (d, J = 8.1 Hz, 1 H), 7.65 (t, J = 7.6
Hz, 1 H), 7.50 (d, J = 7.6 Hz, 1 H), 7.22 (t, J = 8.1 Hz, 1 H), 7.01 (s, 1 H),
6.78 (d, J = 7.6 Hz, 1 H), 6.64 (d, J = 8.1 Hz, 1 H), 6.07 (br s, 2 H), 2.63 (s,
3 H), 2.55 (s, 3 H), 2.50 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 158.5, 145.5, 144.3, 144.5, 135.1,
131.9, 130.0, 130.1, 129.2, 126.5, 126.3, 122.5, 122.0, 121.2, 117.4,
21.7, 20.3, 18.9.
MS (ESI): m/z = 411 [M + H+].
Anal. Calcd for C22H22N2O6: C, 64.38; H, 5.40; N, 6.83. Found: C, 64.52;
H, 5.35; N, 6.77.
MS (ESI): m/z = 263 [M + H+].
Anal. Calcd for C18H18N2: C, 82.41; H, 6.92; N, 10.68. Found: C, 82.25;
H, 6.96; N, 10.80.
2-Methoxy-6-(8-methoxy-4-methyl-6-tritylquinolin-2-yl)-4-tri-
tylaniline (2o)
Yield: 498 mg (64%); colorless solid; mp 144–146 °C.
3-(4,6-Dimethyl-1,8-naphthyridin-2-yl)-5-methylpyridin-2-amine
(2s)
IR (KBr): 3375, 2989, 1601, 1165, 920, 781 cm–1
.
Yield: 137 mg (52%); yellow solid; mp 227–229 °C.
1H NMR (500 MHz, CDCl3): δ = 7.90 (s, 1 H), 7.78–7.67 (m, 7 H), 7.55
(s, 1 H), 7.52–7.35 (m, 12 H), 7.31–7.24 (m, 6 H), 7.20–7.12 (m, 6 H),
7.01 (s, 1 H), 6.99 (s, 1 H), 6.96 (s, 1 H), 5.99 (br s, 2 H), 3.89 (s, 3 H),
3.85 (s, 3 H), 2.64 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 155.5, 149.6, 148.6, 144.4, 138.1,
136.4, 135.8, 132.9, 130.3, 129.7, 126.6, 125.8, 122.9, 122.5, 121.8,
121.5, 120.8, 120.1, 117.1, 111.9, 111.1, 102.6, 64.9, 64.3, 55.5, 54.9,
19.8.
IR (KBr): 3444, 2975, 1311, 947, 729 cm–1
.
1H NMR (500 MHz, DMSO-d6): δ = 8.99 (s, 1 H), 8.41 (s, 1 H), 7.80 (s, 1
H), 7.34 (s, 1 H), 7.01 (s, 1 H), 4.62 (br s, 2 H), 2.42 (s, 3 H), 2.37 (s, 3
H), 2.35 (s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 153.6, 150.8, 150.3, 149.9, 147.2,
146.5, 135.0, 134.3, 133.8, 123.9, 121.2, 115.1, 112.3, 21.1, 18.9, 18.7.
MS (ESI): m/z = 265 [M + H+].
MS (ESI): m/z = 779 [M + H+].
Anal. Calcd for C16H16N4: C, 72.70; H, 6.10; N, 21.20. Found: C, 72.97;
H, 6.13; N, 20.90.
Anal. Calcd for C56H46N2O2: C, 86.34; H, 5.95; N, 3.60. Found: C, 85.99;
H, 6.00; N, 3.66.
3-(4-Methyl-6-nitro[1,8]naphthyridin-2-yl)-5-nitropyridin-2-yl-
amine (2t)
Methyl 2-[2-Amino-5-(methoxycarbonyl)-3-methylphenyl]-4,8-
dimethylquinoline-6-carboxylate (2p)
Yield: 134 mg (41%); yellow solid; mp 251–253 °C.
Yield: 280 mg (74%); yellow solid; mp 174–176 °C.
IR (KBr): 3450, 2961, 1599, 1400, 1218, 950, 715 cm–1
.
IR (KBr): 3401, 2988, 1599, 1175, 928, 791 cm–1
.
1H NMR (500 MHz, DMSO-d6): δ = 9.04 (s, 1 H), 8.83 (s, 1 H), 7.70 (s, 1
H), 7.52 (s, 1 H), 6.70 (s, 1 H), 4.57 (br s, 2 H), 2.46 (s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 163.3, 147.0, 139.3, 135.8, 134.5,
132.6, 132.0, 131.9, 129.3, 129.2, 125.1, 103.2, 100.5, 20.6.
1H NMR (500 MHz, CDCl3): δ = 8.13 (s, 1 H), 8.01 (s, 1 H), 7.79 (s, 1 H),
7.44 (s, 1 H), 7.05 (s, 1 H), 3.95 (s, 3 H), 3.89 (s, 3 H), 2.66 (s, 3 H), 2.25
(s, 3 H), 2.20 (s, 3 H).
13C NMR (125 MHz, CDCl3): δ = 168.8, 167.9, 156.8, 156.5, 150.1,
148.2, 137.9, 130.0, 127.1, 125.7, 122.8, 121.6, 120.5, 120.3, 117.7,
53.2, 51.4, 20.1, 19.1, 17.7.
MS (ESI): m/z = 327 [M + H+].
Anal. Calcd for C14H10N6O4: C, 51.54; H, 3.09; N, 25.76. Found: C,
51.75; H, 3.00; N, 25.68.
MS (ESI): m/z = 379 [M + H+].
© Georg Thieme Verlag Stuttgart · New York — Synthesis 2016, 48, A–J