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S. Kuhl et al. / Journal of Organometallic Chemistry 690 (2005) 6169–6177
4.3.2. N,N0-di(2,4-dimethylphenyl)-1,4-benzenediamine
(16)
6.49 (dd, J = 8.4, 2.0 Hz, 2H), 5.93 (s, 4H), 5.22 (brs,
NH), 2.29 (s, 6H); 13C NMR (100 MHz, CDCl3): d 145.5,
139.3, 138.7, 137.1, 130.3, 126.1, 125.6, 121.8, 115.3,
108.1, 106.2, 98.5, 98.4, 16.3. IR (KBr, cmꢀ1):
mNH = 3427. Anal. Calc. for C28H24N2O4: C, 74.32; H,
5.35; N, 6.19; O, 14.14. Found: C, 74.57; H, 5.47; N, 6.24%.
The title compound was isolated as a beige solid in 82%
yield after column chromatography using AcOEt/hexane
1
3:97 as eluant, m.p. 129 ꢀC. H NMR (400 MHz, DMSO-
d6): d 6.99 (d, J = 7.2 Hz, 2H), 6.93 (brs, NH), 6.91 (s,
4H), 1.72 (brs, 2H), 6.57 (d, J = 7.2 Hz, 2H), 2.17 (s,
6H), 2.16 (s, 6H); 13C NMR (100 MHz, DMSO-d6): d
142.9, 137.2, 135.1, 130.4, 123.4, 120.4, 119.7, 116.7, 20.8,
17.5. IR (KBr, cmꢀ1): mNH = 3378. MS (EI) 316. Anal.
Calc. for C22H24N2: C, 83.50; H, 7.64; N, 8.85. Found:
C, 83.15; H, 7.83; N, 8.80%.
4.3.7. N-{2-methyl-4-[3-methyl-4-(3-
pyridylamino)phenyl]phenyl}-3-pyridinamine (22)
The title compound was isolated as a clear brown solid
in 95% yield after column chromatography using MeOH/
1
AcOEt 10:90 as eluant, m.p. 62 ꢀC. H NMR (400 MHz,
DMSO-d6): d 8.28 (brs, 2H), 7.97 (brd, J = 2.8 Hz, 2H),
7.65 (brs, 2H), 7.50 (brs, 2H), 7.39 (brd, J = 8.0 Hz, 2H),
7.23 (brs, 2H), 7.22 (brs, 2H), 7.18–7.13 (m, 2H), 2.29 (s,
6H); 13C NMR (100 MHz, DMSO-d6): d 140.8, 139.0,
138.6, 138.0, 133.6, 129.5, 128.2, 123.7, 123.0, 121.0,
119.5, 17.5. IR (KBr, cmꢀ1): mNH = 3244. MS (EI) 366.
Anal. Calc. for C24H22N4: C, 78.66; H, 6.05; N, 15.29.
Found: C, 78.43; H, 6.27; N, 15.36%.
4.3.3. N,N0-diphenyl-1,3-benzenediamine (17)
The title compound was isolated as a clear brown solid
in 89% yield after column chromatography using AcOEt/
1
hexane 5:95 as eluant, m.p. 104 ꢀC. H NMR (400 MHz,
CDCl3): d 7.24 (ddd, J = 8.0, 8.0, 1.2 Hz, 4H), 7.11
(dd, J = 8.0, 8.0 Hz, 1H), 7.04 (d, J = 8.0 Hz, 4H), 6.90
(dd, J = 8.0 Hz, 2H), 6.71 (dd, J = 2.4 Hz, 1H), 6.60 (dd,
J = 8.0, 2.4 Hz, 2H); 13C NMR (100 MHz, CDCl3): d
144.8, 143.3, 130.6, 129.7, 121.5, 118.7, 110.6, 106.7. IR
(KBr, cmꢀ1): mNH = 3365. MS (EI) 260. Anal. Calc. for
C18H16N2: C, 83.04; H, 6.19; N, 10.76. Found: C, 83.20;
H, 6.30; N, 10.84%.
4.3.8. N-phenyl-4-(4-anilinobenzyl)aniline (23)
The title compound was isolated as a white solid in 96%
yield after column chromatography using AcOEt/hexane
1
5:95 as eluant, m.p. 120 ꢀC. H NMR (400 MHz, CDCl3):
d 7.22 (ddd, J = 7.2, 7.2, 1.2 Hz, 4H), 7.08 (d, J = 8.4 Hz,
4H), 7.00 (dd, J = 7.2, 1.2 Hz, 4H), 6.99 (d, J = 8.4 Hz,
4H), 6.87 (dd, J = 7.2, 7.2 Hz, 2H), 5.61 (brs, NH), 3.86
(s, 2H); 13C NMR (100 MHz, CDCl3): d 141.9, 139.2,
131.2, 127.3, 127.0, 117.1, 115.4, 114.2, 40.8. IR (KBr,
mNH = 3389. MS (EI) 350. Anal. Calc. for
C25H22N2: C, 85.68; H, 6.33; N, 7.99. Found: C, 85.70;
H, 6.45; N, 7.83%.
4.3.4. N-phenyl-4-(4-anilinophenyl)aniline (19)
The title compound was isolated as a brown waxy solid
in 95% yield after column chromatography using AcOEt/
hexane 3:97 as eluant. 1H NMR (400 MHz, CDCl3): d
7.25–7.15 (m, 8H), 7.10–6.85 (m, 10H); 13C NMR
(100 MHz, CDCl3): d 147.7, 142.7, 132.2, 129.1, 128.9,
125.3, 123.6, 122.6, 122.8, 121.9, 118.4. IR (KBr, cmꢀ1):
cmꢀ1):
m
NH = 3393. MS (EI) 336. Anal. Calc. for C24H20N2: C,
85.68; H, 5.99; N, 8.33. Found: C, 85.55; H, 6.06; N, 8.52%.
4.3.9. N-phenyl-4-(4-anilinophenoxy)aniline (24)
The title compound was isolated as a clear brown solid
in 98% yield after column chromatography using AcOEt/
4.3.5. N-phenyl-4-(4-anilino-3-methylphenyl)-2-
methylaniline (20)
1
hexane 10:90 as eluant, mp 123 ꢀC. H NMR (400 MHz,
The title compound was isolated as a clear brown solid
in 95% yield after column chromatography using AcOEt/
hexane 3:97 as eluant, m.p. 123 ꢀC. H NMR (400 MHz,
CDCl3): d 7.45 (brs, 2H), 7.39–7.30 (m, 4H), 7.25–7.12
(m, 4H), 6.94 (d, J = 7.6 Hz, 4H), 6.75 (dd, J = 7.6,
7.6 Hz, 2H), 2.28 (s, 6H); 13C NMR (100 MHz, CDCl3):
d 144.3, 139.70, 132.9, 128.9, 128.5, 128.0, 123.5, 119.1,
118.3, 115.7, 17.71. IR (KBr, cmꢀ1): mNH = 3405. MS
(EI) 364. Anal. Calc. for C26H24N2: C, 85.68; H, 6.64; N,
7.69. Found: C, 85.60; H, 6.83; N, 7.51%.
DMSO-d6): d 8.03 (brs, NH), 7.19 (dd, J = 7.2, 7.2 Hz,
4H), 7.11 (d, J = 8.4 Hz, 4H), 7.03 (d, J = 8.4 Hz, 4H),
6.92 (d, J = 7.2 Hz, 4H), 6.77 (dd, J = 7.2, 7.2 Hz, 2H);
13C NMR (100 MHz, DMSO-d6): d 150.3, 143.6, 138.0,
128.5, 118.5, 118.4, 118.3, 115.1. IR (KBr, cmꢀ1):
1
m
NH = 3403. MS (EI) 352. Anal. Calc. for C24H20N2O: C,
81.79; H, 5.72; N, 7.95; O, 4.54. Found: C, 81.65; H,
5.60; N, 7.83%.
4.3.10. N-{4-[4-(3-methoxyanilino)phenoxy]phenyl}-3-
methoxyaniline (25)
4.3.6. N-[4-(4-benzo[d][1,3]dioxol-5-ylamino-3-
methylphenyl]-2- methylphenyl]benzo[d] [1,3]dioxol-5-
amine (21)
The title compound was isolated as a brown solid in 82%
yield after column chromatography using AcOEt/hexane
30:70 as eluant, m.p. 218 ꢀC. 1H NMR (400 MHz, CDCl3):
d 7.31 (brs, 2H), 7.29 (dd, J = 8.4, 2.0 Hz, 2H), 7.09 (d,
J = 8.4 Hz, 2H), 6.74 (d, J = 8.0 Hz, 2H), 6.64 (brs, 2H),
The title compound was isolated as a yellow solid in 89%
yield after column chromatography using AcOEt/hexane
20:80 as eluant, m.p. 81–82 ꢀC. 1H NMR (400 MHz,
DMSO-d6): d 8.07 (brs, NH), 7.16 (d, J = 8.4 Hz, 4H),
7.13 (dd, J = 8.0, 8.0 Hz, 2H), 6.96 (d, J = 8.4 Hz, 4H),
6.66 (d, J = 8.0 Hz, 2H), 6.63 (brs, 2H), 6.37 (d,
J = 8.0 Hz, 2H), 3.72 (s, 6H); 13C NMR (100 MHz,
DMSO-d6): d 160.7, 151.4, 146.0, 138.8, 130.2, 120.0,