HEMICAL News:
Dec. 30, 1881,

On Beta-Lutidine.

307
~~ The preparation of A-lutidine in a state of purity is a
work of much labour. On distilling cinchonine with hydrate
 of potassium a mixture of at least ten alkaloids is
wbtained, and the A-lutidine has to be separated by fracsonal
 distillation. I have, however, prepared for the pursoses
 of this investigation probably the largest quantity of
che base that has yet obtained—rather more than half a
pint.

THE CHEMICAL NEWS.

VoL. XLIV. No. 1153,

ON B-LUTIDINE.*
8y C. GREVILLE WILLIAMS, F.R.S.

Action of Sodium upon f-Lutidine,
I found that by the a&ion of sodium upon chinoline it
became polymerised with the formation of a body having
the composition of dichinoline. This substance forms a
crystalline hydrochlorate, having, when freshly prepared,
3 magnificent scarlet colour,* The hydrochlorate of
lichinoline dyes silk a brilliant but fugitive orange
colour. This reaction, namely, the formation of a
coloured hydrochlorate from a colourless oily base, being
srobably unique, it became desirable to ascertain how glutidine
 would behave under similar circumstances.
Fragments of sodium were added to A-lutidine in the
cold ; they acquired a brilliant yellow colour, and had
exactly the appearance of pieces of metallic gold. The
mixture was then warmed until the sodium melted ; it wag
then removed from the lamp. A violent rea&ion ensued,
and the whole turned greenish black by refleéted light, and
yellowish brown by transmitted light. The -produ& was
eft until the next day, and was then boiled for five
ninutes ; it thickened, and, on being poured into water,
vielded a heavy brown oil. No pyrrol was formed. Exess
 of hydrochloric acid being added, the oil dissolved,
forming a brown solution; this was fractionally precipi-:ated
 with solution of platinic chloride, Six precipitates
were obtained ; the first was pale brown, the second fawn
scloured, the third a paler fawn, the fourth Naples yellow,
‘he fifth sulphur yellow. The last only was distinctly
:rystalline under the lens. If put in a wet state into the
water-oven they melt, but if first dried over sulphuric
acid the desiccation may be completed without fusion.
[he platinum was determined separately in the first
our precipitates; the fifth and sixth were so small in
quantity that they had to be mixed.

IN the Bulletin of the Chemical Society of Paris for June 3,
1880, there appears a notice of a paper read before the
Russian Chemical Society, by MM. Boutlerow and
Wischnegradsky, in wkich they state, among other
things, that by the a&ion of alkalies on cinchonine they
had obtained quinoline (chinoline) almost pure, and a
volatile colourless liquid alkaloid boiling constantly at
166°, having the formula C,HgN, and which they” say
appears to be identical with the base obtained by me in
distilling cinchonine with potash, and also with the lutidine
of Anderson. Of the identity of the base obtained by them
with 8-lutidine there can ba no doubt, the boiling-point
(166°) given by them being to half a degree the mean of
the range (163° to 168°) given by me in my * Researches
on Isomeric Alkaloids.” +
With regard to the identity which they assume between
tutidine and B-lutidine, it is evident that they have not
seen my paper last quoted, or they would hardly have
ignored the mass of fads which I have adduced to prove
the isomerism, and not identity, of the two bases.
In the Bulletin of the Chemical Society of Paris, Nos. 5
and g, for September 5, 1880, p. 210, M. W. Oechsner de
Coninck publishes an investigation on the lutidine, collidine,
 and parvoline obtained as above from cinchonine,
ais only reference to my work being to the Ann. Chim.
Phys., xlv., p. 488, in which he says that I have shown
the presence of a base possessing the composition of lutidine.
 He then proceeds to give analyses, density, and
vapour-densities of S-lutidine, apparently unaware that
they were simply repetitions of what I had done many
years before. I gave the analysis of the base and the
platinum salt in the Z'vans. Roy. Soc. Edin., previously
quoted. also gave the analyses of the platinum salt of
collidine in the same paper. The specific gravity of
3-lutidine at oc was given by me in my ‘* Researches on
[someric Alkaloids* as 0°9555; M. de Coninck makes it
2°¢5035 at the same temperature. M. de Coninck gives
the vapour-density as determined in Von Meyer's appar--us
 as 3-80; I gave it as 365 in two experiments exactly
agreeing with each other, and also made in Von Meyer's
apparatus.) The formula C,HgN requires 3'699. In my
paper ‘* On Isomeric Alkaloids” I gave as the result of a
determination by Dumas’s method 3-787. M. de Coninck
also states as a new result that the platino-chloride of the
lutidine from cinchonine is modified by hot water, losing
two molecules of hydrochloric acid, The extraordinary
difference Letween the decomposability of the platinum
salts of lutidine and g-lutidine on boiling with water, with
evolution of hydrochloric acid, was one of the numerous
illustrations of the isomerism of the two bases which 1
adduced in my * Researches on Isomeric Alkaloids
seventeen years ago. The tone of M. de Coninck’s
papers shows that he believes his results to be entirely
new. I mention the above fads partly because they are
facts, but chiefly as showing that other chemists are
working on A-lutidine, and that it therefore becomes necessary
 to publish my more recent experiments somewhat
earlier than I should otherwise have done.
* A Paper read before the Royal Society, December 15,1881,
t Proc;Roy. Soc., vol. xiii., p. 305, June, 1864.
{ This is a précis of my paper, “On the Voiatile Bases produced by
Destructive Distillation of Cinchonine,” Trans. Roy. Soc. Edinburgh,
kxi., part 2, April, 1855.
| CHEMICAL NEws, March, 1879,

Number of Precipitate. - Percentage of Platinum.
Loo vo vo wl al 25°28
Loo oo se ee 24°82
ar... .. 26°40
Ive. 27°57
V.and VI. 0°28

The second precipitate, in its percentage of platinum,
igees with the formula for the platinum salt of the hydrochlorate
 of di-beta-lutidine containing 2 molecules of diseta-lutidine,
 the formula being—
2(Cy4HgN,) HCI PLC,
or, of a still higher polymer, in which casé the formula
becomes—
C28H36N, HCL PtCl, 3 ’
whichever formula we adopt, the percentage of platinum
required is 24°61, which agrees closely with the experimental
 number. The other precipitates were probably
mixtures of this salt with the platinum salt of di-beta.
lutiding
Ci14H18N,. HCLPLCI,,
which requires 33°53 per cent of platinum,
A second preparation was then made, but the oj] ob-:ained
 on treating the crude produc with water was distilled;
the boiling-point varied from 180°C, to a temperature
above the range of the mercurial thermometer, Four
fractions were received, the fourth, which distilled at and
above 300°, was dissolved in hydrochloric acid, and frac.
:ionally precipitated with platinic chloride.

————— -. ——————
* CreMicaL News, March 1, 1878; Proc. Roy. So6., No, 211, 1881.