160 



Mr. C. G. Williams. 



[Dec. 15, 



from cinchonine is modified by hot water, losing two molecules of 

 hydrochloric acid. The extraordinary difference between the decom- 

 posability of the platinum salts of lutidine and /S-lutidine on boiling 

 with water with evolution of hydrochloric acid, was one of the numer- 

 ous illustrations of the isomerism of the two bases which I adduced in 

 my " Researches on Isomeric Alkaloids " seventeen years ago. The 

 tone of M. de Coninck's paper shows that he believes his results to 

 be entirely new. I mention the above facts partly because they are 

 facts, but, chiefly as showing that other chemists are working on /3- 

 lutidine, and that it therefore becomes necessary to publish my more 

 recent experiments somewhat earlier than I should otherwise have 

 -done. 



The preparation of /3-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 obtained, and the /3-lutidine has to be 

 separated by fractional distillation. I have, however, prepared for 

 the purposes of this investigation probably the largest quantity of the 

 base that has yet been obtained — rather more than half a pint. 



Action of Sodium upon ft-Lutidine. 



I found that by the action 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, a magnificent scarlet colour.* The hydro- 

 chlorate of dichinoline dyes silk a brilliant but fugitive orange colour. 

 This reaction, namely, the formation of a coloured hydrochlorate from 

 a colourless oily base, being probably unique, it became desirable to 

 ascertain how /3-lutidine would behave under similar circumstances. 



Fragments of sodium were added to /3-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 was then removed from the lamp. A violent 

 reaction ensued, and the whole turned greenish-black by reflected 

 light, and yellowish-brown by transmitted light. The product was 

 left until the next day, and was then boiled for five minutes ; it 

 thickened, and, on being poured into water, yielded a heavy brown 

 oil. No pyrrol was formed. Excess of hydrochloric acid being added, 

 the oil dissolved, forming a brown solution; this was fractionally 

 precipitated with solution of platinic chloride. Six precipitates 

 were obtained ; the first was pale brown, the second fawn-coloured, 

 the third a paler fawn, the fourth Naples yellow, the fifth sulphur- 

 yellow. The last only was distinctly crystalline under the lens. If 

 put in a wet state into the water-oven they melt, but, if first dried over 



* " Chemical News," March 1, 1878 ; " Proc. Roy. Soc," vol. 31, p. 536. 



