696
DIKUSAR
absorption bands and the proton signals confirming the
presence of the structural fragments R are observed.
A solution of 5 mmol of azomethine IIIa–IIIz,
10 mmol of NaBH4, and 30 mmol of glacial acetic acid
in 50 ml of anhydrous ether was left for 18–20 h at 20–
25°C. The solution was washed with water and 5%
NaHCO3 solution, the solvent was removed in a
vacuum. The residue was purified by recrystallization
from a benzene–hexane mixture or by column chromato-
graphy on silica gel (100–160 μm, eluent benzene).
EXPERIMENTAL
IR spectra of the compounds were recorded on a
FTIR Protégé-Nicolet 460 spectrophotometer from a
1
thin layer or KBr pellets, H NMR spectra were taken
on a Tesla BS-587A spectrometer (100 MHz) from 5%
solutions in deuterochloroform, the chemical shifts
were determined with respect to the internal TMS.
Molecular mass was determined by cryoscopy in benzene.
Diamines (IVaa–IVcc). A solution of 5 mmol of a
bisazomethine IIIaa–IIIcc, 20 mmol of NaBH4, and
60 mmol of glacial acetic acid in 100 ml of anhydrous
ether was left for 18–20 h at 20–25°C. Target products
were purified by recrystallization from a benzene–
hexane mixture.
For the study was used 2-hydroxy-3-methoxy-
benzaldehyde I of “pure” grade, 99% of the main pro-
duct, mp 41–42°C.
REFERENCES
(E)-2-Methoxy-6-(R-imino)methylphenols (IIIa-
IIIz). A solution of 5 mmol of 2-hydroxy-3-methoxy-
benzaldehyde I and 5 mmol of the corresponding
monoamine IIa-IIz in 40 ml of anhydrous methanol
was refluxed for 30–45 min. The solution was cooled
to 0–5°C, the precipitated crystals of an azomethine
were filtered off on a porous glass filter, washed with
cold methanol, and air-dried for 6–8 h. Glassy
azomethines were separated by decantation, the final
purification was performed by column chromato-
graphy on neutral alumina, 40–100 μm, II degree
activity by Brockmann, eluent dichloromethane.
1. Trivedi, S.D., Kubawat, H.T., and Parekh, H.H.,
J. Indian Chem. Soc., 2002, no. 3, p. 282.
2. Yuzhik, L.I., Antonovskaya, L.I., Belyasova, N.A.,
Basalaeva, L.I., and Tarasevich, V.A., Abstract of
Papers, 22 Int. Conf. “Chemicals, Reagents, and the
Process of Low-Tonnage Chemistry” (Reaktiv-2009),
Ufa, November 23–25, 2009, p. 87.
3. Dikusa,r E.A., Zh. Obshch. Khim., 2008, vol. 78, no. 4,
p. 642.
4. Dikusar, E.A., Kozlov, N.G., and Potkin, V.I., Zh.
Obshch. Khim., 2008, vol. 78, no. 6, p. 969.
5. Esteves-Souza, A., Echevarria, A., and Sant’Anna, C.M.R.,
Bisazomethines (IIIaa–IIIcc). A solution of 10 mmol
of 2-hydroxy-3-methoxybenzaldehyde I and 5 mmol of
a diamine II in 50 ml of anhydrous methanol was
refluxed for 45 min. Target products were isolated
similarly to the azomethines IIIa–IIIz.
Quim. Nova, 2004, vol. 27, p. 72.
6. Dyer, J.A., Applications of Absorption Spectroscopy of
Organic Compounds, Moscow: Khimiya, 1970, p. 92.
7. Desiraju, G.R. and Steiner, T., The Weak Hydrogen
Bond in Structural Chemistry and Biology, Oxford
University Press (U.S.), 2001.
2-Methoxy-6-(R-amino)methylphenols (IVa–IVz).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 82 No. 4 2012
Dikusar
