Platinum(II) Complexes
775
m ixture was stirred overn igh t. Th e m ixture was th en filtered th rough Celite filter an d th e
filter was wash ed with eth an ol (10 m l). Th e filtrate was reduced in volum e to 10 m l an d
h exan e (50 m l) was added. Th e precipitate was collected on a glass filter an d dried in vacuo
to yield 3.62 g (53%) of a yellow powder. 1H NMR (300.13 MHz, CD2Cl2): 8.79 (s, 1 H,
3
3
N=CH), 8.00 (d, JHH = 7.8, 1 H, pyH), 7.71 (t, JHH = 7.5, 1 H, pyH), 7.51 (br s, 1 H, OH),
3
4
3
4
7.41 (dd, JHH = 7.8, JHH = 1.5, 1 H, ArH), 7.24 (m , 2 H, ArH), 7.01 (dd, JHH = 8.1, JHH
=
1.5, 1 H, ArH), 6.94 (dt, JHH = 7.8, JHH = 1.2, 1 H, ArH), 2.60 (s, 3 H, CH3). 13C NMR
(75.47 MHz, aceton e-d6): 159.0, 158.7, 154.6, 153.2, 138.3, 137.8, 137.2, 136.2, 129.5, 125.0,
120.3, 119.1, 117.6, 116.1, 23.8.
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4
2-[(2-Pyridin ylm eth yliden e)am in o]ph en ol (3ba)
Pyridin e-2-carbaldeh yde (3.49 g, 32.6 m m ol) an d 2-am in oph en ol (3.56 g, 32.6 m m ol) were
dissolved in m eth an ol (50 m l). 3 Å m olecular sieve was added to th e solution an d th e m ix-
ture was stirred overnight. The solid was filtered off and extracted twice with m ethanol (150 m l).
Th e volatiles of th e com bin ed filtrates were rem oved by rotary evaporation , yieldin g 7.0 g of
a brown oil. Th e oil was dissolved in m eth an ol (15 m l), an d dieth yl eth er (200 m l) was
added to precipitate th e product. Th e yellow solid was filtered off on a glass filter an d
wash ed with dieth yl eth er (3 × 20 m l). Th e solid was dried in vacuo to yield 2.48 g (38%) of
a yellow powder. 1H NMR (300.13 MHz, CD2Cl2): 8.85 (s, 1 H, N=CH), 8.71 (m , 1 H, pyH),
3
3
4
3
8.23 (d, JHH = 8.1, 1 H, pyH), 7.85 (dt, JHH = 7.8, JHH = 1.5, 1 H, pyH), 7.43 (dt, JHH = 7.5,
4JHH = 1.2, 1 H, ArH), 7.40 (dd, JHH = 7.5, JHH = 1.2, 1 H, ArH), 7.38 (br s, 1 H, OH), 7.25
(dt, JHH = 7.8, JHH = 1.5, 1 H, ArH), 7.01 (dd, JHH = 8.4, JHH = 1.5, 1 H, ArH), 6.95 (dt,
3JHH = 7.7, JHH = 1.2, 1 H, ArH). 13C NMR (75.47 MHz, aceton e-d6): 158.7, 155.2, 153.2,
3
4
3
4
3
4
4
150.0, 137.0, 136.2, 129.6, 125.7, 122.0, 120.3, 117.7, 116.2.
1-Meth oxy-2-[(2-pyridylm eth yliden e)am in o]eth an e (3bb)
Pyridin e-2-carbaldeh yde (5 m l, 53 m m ol) an d 2-(m eth oxyeth yl)am in e (10 m l, 115 m m ol)
were placed togeth er with 3 Å m olecular sieve in a roun d-bottom flask at room tem perature.
After stirrin g th is m ixture for 30 m in , th e sieve was filtered off an d wash ed with h exan e.
Th e volatiles were rem oved in vacuo to yield 8.5 g (98%) of a yellow oil. 1H NMR (300.13
3
MHz, CDCl3): 8.30 (d, 1 H, pyH), 8.09 (s, 1 H, im H), 7.67 (d, JH3H = 7.5, 1 H, pyH), 7.37 (t,
3
3JHH = 7.5, 1 H, pyH), 6.94 (“t”, JHH = 4.8, 1 H, pyH), 3.52 (t, JHH = 5.4, NCH2), 3.38 (t,
3JHH = 5.4, 1 H, OCH2), 7.03 (s, 3 H, CH3). 13C NMR (75.47 MHz, CDCl3): 163.3, 154.4,
149.3, 124.7, 121.3, 71.8, 60.8, 58.7.
4-Meth yl-2-[(2-pyridylm eth yliden e)am in o]ph en ol (3bc)
2-Am in o-4-m eth ylph en ol (2.56 g, 20.8 m m ol), pyridin e-2-carbaldeh yde (2.31 g, 21.6 m m ol)
an d a 3 Å m olecular sieve were suspen ded in toluen e (50 m l). Th is m ixture was stirred at
100 °C for 90 m in . Th e m olecular sieve was filtered off an d wash ed with toluen e (20 m l).
Th e volatiles were rem oved by rotary evaporation to yield 5.10 g of a red-brown oil. Th e oil
was crystallized from THF/h exan e to yield 1.38 g (39%) of yellow n eedles. 1H NMR (300.13
3
3
MHz, CDCl3): 8.81 (s, 1 H, im H), 8.72 (d, JHH = 4.8, 1 H, pyH), 8.19 (d, JHH = 7.8, 1 H,
3
4
3
3
4
pyH), 7.82 (dt, JHH = 7.5, JHH = 1.2, 1 H, pyH), 7.37 (ddd, JHH = 7.2, JHH = 4.5, JHH = 0.9,
3
4
3
1 H, pyH), 7.20 (br s, 1 H, ArH), 7.05 (dd, JHH = 8.4, JHH = 1.2, 1 H, ArH), 6.92 (d, JHH
=
Collect. Czech. Chem. Commun. 2007, Vol. 72, Nos. 5–6, pp. 764–784