349
ELECTROPHILIC TROPYLATION OF 2-AMINOPYRIDINE
N-(Triphenylmethyl)pyridin-2-amine (6). Triphenyl-
carbenium perchlorate (5), 0.78 g (2.3 mmol), was
added to a solution of 0.19 g (1 mmol) of N-(cyclo-
hepta-2,4,6-trien-1-yl)pyridin-2-amine (3) in 7 mL of
methylene chloride, and the mixture was refluxed for
2 h. The precipitate was filtered off and washed with
methylene chloride (4 mL), the filtrate was neutralized
with 10% aqueous ammonia to pH 7, and the
precipitate was filtered off, washed with diethyl ether,
and dried. Yield 0.20 g (60%), mp 146–148°C (from
EtOH). 1H NMR spectrum (CDCl3), δ, ppm: 5.79–5.82
d (1H, 3-H, J = 8.7 Hz), 6.14 s (1H, NH), 6.45–6.49 m
(1H, 4-H), 6.99–7.04 m (1H, 5-H), 7.17–7.35 m (15N,
Ph), 8.00–8.02 d (1H, 6-H, J = 6.0 Hz). Mass spec-
trum, m/z (Irel, %): 336 (25.5) [M]+, 243 (100.0), 165
(48.2), 78 (9.2).
at 295(2) K: a = 13.376(3), b = 9.606(2), c = 14.772(4) Å;
β = 103.24(3)°; V = 1847.6(8) Å3; dcalc = 1.209 g/cm3;
µ = 0.071 mm–1; Z = 4; λ(MoKα) 0.71073 Å. Final
divergence factors: R1 = 0.0489, wR2 = 0.1199 [3137
reflections with I > 2σ(I)]; R1 = 0.0725, wR2 = 0.1338
(4366 independent reflections); goodness of fit S =
1.064.
The crystallographic data for compounds 3 and 6
were deposited to the Cambridge Crystallographic
Data Centre [CCDC entry nos. 1 488 927 (3),
1 488 928 (6)].
ACKNOWLEDGMENTS
The authors thank S.Yu. Balandina (Bakteritsid
Research Laboratory, Perm State National Research
University) for performing antibacterial tests.
1
The H NMR spectra were recorded on Varian
Mercury 300BB (300 MHz) and Bruker Avance III HD
(400 MHz) spectrometers using hexamethyldisiloxane
was internal standard. The mass spectra (electron
impact, 70 eV) were obtained on an Agilent Techno-
logies 6890N/5975B GC/MS system; HP-5ms column,
30 m × 0.25 mm, film thickness 0.25 μm; carrier gas
helium; oven temperature 100°C, injector temperature
260, 270°C.
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6.4891(17) Å; β = 90.635(16)°; V = 2047.1(11) Å3;
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twinnig matrix [–1 0 0, 0 1 0, 0 0 –1]. Final divergence
factors: R1 = 0.0494, wR2 = 0.1037 [1624 reflections
with I > 2σ(I)]; R1 = 0.0732, wR2 = 0.1203 (2348
independent reflections); goodness of fit S = 1.022; twin
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 87 No. 2 2017