Chemistry of Heterocyclic Compounds, Vol. 42, No. 1, 2006
NOVEL METHOD FOR SYNTHESIS
OF 3-HYDROXY-1-PHENYL-
1,2,3,4-TETRAHYDROQUINOLINE
B. Barvainiene, A. Stanisauskaite, and V. Getautis
Keywords:
3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline,
N-(2,3-epoxypropyl)diphenylamine,
epichlorohydrin, cyclization.
When diphenylamine is heated with epichlorohydrin under pressure [1] or with addition of sodium
iodide at high temperatures [2], 3-hydroxy-1-phenyl-1,2,3,4-tetrahydroquinoline (1) is formed. In [3], it was
obtained by heating diphenylamine with excess epichlorohydrin at atmospheric pressure without a catalyst. The
same authors proved that formation of compound 1 occurs via N-(3-chloro-2-hydroxypropyl)diphenylamine [4].
We have observed that tetrahydroquinoline 1 can also be obtained in 53% yield from the epoxypropyl
derivative of diphenylamine.
O
OH
220–225 oC
N
N
1
When N-(2,3-epoxypropyl)diphenylamine synthesized by reaction of diphenylamine and
epichlorohydrin in the presence of KOH was distilled under vacuum, we noted formation of a byproduct with
melting point (78-79°C) corresponding to the melting point of the known compound 1 [3]. The optimal
cyclization temperature is 220-225°C; raising the temperature reduces the yield of the cyclization product 1. In
1
order to unambiguously establish its structure, we took the H NMR, IR, and mass spectra, since these data are
not available in the literature.
1
The H NMR spectrum was recorded on a Gemini-2000 (300 MHz), internal standard TMS. The IR
spectrum was taken on a UR-20 spectrometer in a KBr disk. The mass spectrum was recorded on a Waters
ZQ-2000 with direct injection of the sample. The course of the reaction was monitored by TLC on Silufol
UV-254 plates in a 1:4 acetone–hexane system. Silica gel L 40/100 (Chemapol) was used for column
chromatography.
__________________________________________________________________________________________
Kaunas University of Technology, Organic Chemistry Department, Kaunas LT-50270, Lithuania;
e-mail: brone.barvainiene@ktu.lt, albina.stanisauskaite@ktu.lt, vytautas.getautis@ktu.lt. Translated from
Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 138-139, January, 2006. Original article submitted
December 2, 2005.
0009-3122/06/4201-0123©2006 Springer Science+Business Media, Inc.
123