Manufacture of Oitrates, Tartrates, and Mandelates of Para-anisidine and Para-phenetidine.
Year: 1895

page_text: Date of Application, 8th June, 1895-Accepted, 7th Sept., 1895
COMPLETE SPECIFICATION.
Manufacture of Oitrates, Tartrates, and Mandelates of Para-anisidine
and Para-phenetidine.
I, Dr. ISRAEL Roos, of 5 Schöne-Aussicht, Frankfurt am Main, Germany,
Chemist, do hereby declare the nature of this invention and in what manner the
same is to be performed to be particularly described and ascertained in and by
the following statement :-
This invention relates to the manufacture of citrates, tartrates and mandelates of
para-anisidine and para-phenetidine.
The invention consists in the reaction of the components upon each other with
or without a convenient solvent liquid and, if necessary, the action of heat. The
compounds obtained by this operation are very useful for medical or technical
purposes.
For instance, the mandelate of para-phenetidine may be obtained in the following
manner:
Equivalent quantities of mandelic acid and para-phenetidine, that is to say the
quantities corresponding to one molecule of each compound are mixed either
directly or in alcoholic solution. If necessary the mixture is heated.
The mixture forms crystals in a short time. After crystallization in water
or another solvent the melting point of the compound is 107° C. The crystals
are bright white laminæ, have no smell, a bitter taste, and may be dissolved in
the ordinary solvents. By the action of alkalies the components are reproduced,
already without heating.
The citrate of para-phenetidine is obtained by mixing the quantities corre-
sponding to three molecules of para-phenetidine and one molecule of citric acid,
directly or in alcoholic solution or in another convenient solvent, with or without
heating the mixture.
The crystals obtained in a short time are crystallized in water or another
solvent. Their melting point is 181° C. (with foaming). The crystals are white
(or rose coloured) prisms, without smell, tasting slightly of citric acid. They are
very soluble in water, less so in alcohol.
By the action of alkalies the components are reproduced.
The tartrate of para-phenetidine is obtained by mixing the quantities corre-
sponding to two molecules of para-phenetidine and one molecule of tartaric acid,
with or without addition of alcohol or another solvent, and, if necessary heating
the mixture. In a short time crystals are formed whose melting point, after
crystallization in water or another solvent, is 213° C. They form beautiful white
needles, are soluble in water, less in alcohol, and are, by the action of alkalies
decomposed into the components. The compound has no smell and tastes slightly
of tartaric acid.
In the same manner the corresponding compounds of para-anisidine are formed
the qualities of which are similar to those of the compounds aforementioned. Their
melting points are:
0802

page_text: Having now particularly described and ascertained the nature of my said inven
and in what manner the same is to be performed, I declare that what
im is:
. A method of manufacturing mandelates, citrates and tartrates of para-anisidin
1 para-phenetidine by mixing equivalent quantities of the components with o
hout addition of alcohol or another convenient solvent and, if necessary, b
ting the mixture, substantially as described.
2. As new articles of manufacture, the citrates, tartrates and mandelates of para
enetidine and para-anisidine, having the formula:
Mandelate of para-anisidinė
melting point 98° C.
=
CH₂OCH NH. CH¸Ó¸
3'
Tartrate of para-anisidine = (C&HOCHÊNH₂) CHÃO
melting point 174° C.
Citrate of para-anisidine = (CHOCHÊNH₂). C¸H¸О„
melting point 187° C.
67
Mandelate of para-phenetidine ==
CHOC,HNH. C,H,O3,
melting point 107° C.
6
Tartrate of para-phenetidine = (CH¸OC₂H¸NH2)2. C¸HO
melting point 213° C.
=
Citrate of para-phenetidine – (C,H,OC,H,NH,). CgHgO,
melting point 181° C.
Dated this 8th day of June 1895.