Journal of Inorganic and General Chemistry
ARTICLE
Zeitschrift für anorganische und allgemeine Chemie
(CH), 110.5 (CH). ESI-MS (+ve ion): found: m/z = 161.2, calcd for
Keywords: Schiff bases; Tin; Coordination chemistry; Quin-
oline; Main group elements
[C9H8N2O + H]+ 161.2 [M + H]+.
5-[(Pyridin-2-ylmethylene)amino]quinolin-8-ol (5): To an open flask
was added 8-hydroxy-5-aminoquinoline (337 mg, 2.1 mmol), 2-for-
mylpyridine (0.20 mL, 2.1 mmol), and ethanol (25 mL). Acetic acid
(two drops) was added and the dark red mixture heated to reflux for
3 h, following which the solvent was removed. The crude product was
purified by recrystallization from ethanol:acetone (3:1, v:v) to obtain
the product as a brown powder. X-ray diffraction quality crystals were
afforded by vapor diffusion of diisopropyl ether into a concentrated
DCM solution of 5. Yield 7% (39.4 mg, 0.15 mmol). 1H NMR
(400 MHz, CDCl3): δ = 8.85 (d, J = 4.2 Hz, 1 H), 8.84 (s, 1 H), 8.77
(s, 1 H), 8.74 (d, J = 4.5 Hz, 1 H), 8.36 (d, J = 7.9 Hz, 1 H), 7.86 (t,
J = 8.4 Hz, 1 H), 7.52 (d, J = 4.9 Hz, 1 H), 7.39 (dd, J = 7.4, 4.9 Hz,
1 H), 7.34 (d, J = 8.2 Hz, 1 H), 7.20 (d, J = 8.2 Hz, 1 H), 5.30 (s, 1
H). 13C{1H} NMR (101 MHz, CDCl3): δ = 159.1 (CH), 155.1 (C),
151.7 (C), 149.9 (CH), 148.6 (CH), 138.9 (C), 138.3 (C), 136.8 (CH),
133.2 (CH), 125.3 (C), 125.2 (CH), 121.9 (CH), 121.9 (CH), 114.3
(CH), 109.9 (CH). HR-ESI (+ve ion): found: m/z = 250.0983; calcd.
for [C15H11N3O + H]+ 250.0980 [M + H]+.
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1
Yield 49% (19.5 mg, 0.03 mmol). H NMR (400 MHz, CDCl3): δ =
8.87 (d, J = 8.4 Hz, 2 H), 8.78 (s, 2 H), 8.72–8.68 (m, 2 H), 8.58–8.54
(m, 2 H), 8.37–8.22 (m, 4 H), 7.80 (t, J = 7.7 Hz, 2 H), 7.57 (d, J =
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calcd. for [C32H26N6O2Sn + H]+ 647.1217 [M + H]+.
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Supporting Information (see footnote on the first page of this article):
Crystallographic data, NMR spectra and diffusion NMR data for all
complexes.
Acknowledgments
The authors would like to thank the ANU Research School of Chemis-
try Analytical Department for all their time and patience throughout
this work.
Received: March 18, 2019
Published Online: April 25, 2019
Z. Anorg. Allg. Chem. 2019, 694–699
© 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim