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a rose-red and, with hydrochloric acid, a pale-yellow coloration. It acts as a powerful poison, diminishing the rate of respiration, and producing paralysis; in these effects, it surpasses apomorphine. V. H. V.

Crystalline Compound from "Kamala." By L. JAWEIN (Ber., 20, 182-183).-Andersen obtained (Jahresber., 1855, 669) from kamala a compound which he described as rottlerin, CH1003. The author, by extracting kamala with carbon bisulphide or benzene, obtained a yellow crystalline substance melting at 200°. It resembles Andersen's compound in its solubility and in giving a red liquid with alkali, but the analytical results do not agree with the formula suggested by Andersen. (Compare A. G. Perkin and W. H. Perkin, this vol., p. 272.)

N. H. M.

Algaborilla. By G. H. HURST (Dingl. polyt. J., 262, 288).—This yellow dye is a species of tannin obtained from the pods yielded by two plants, namely, Prosopis pallida and P. algarobo, which are indigenous in the mountainous regions of South America. 52 to 55 per cent. of the pods consist of soluble matter containing 27-29 per cent. of tannin. Algaborilla forms yellow precipitates with the salts of zinc, antimony, lead, or aluminium, and imparts to cotton or wool mordanted with metallic salts a yellow colour which bears light very well, and resists weak acids. Alkalis change the colour to brown.

D. B.

Indian-yellow and Glycuronic Acid. By E. KÜLZ (Zeit. Biol., 23, 475-485). Baeyer (Annalen, 155, 257) showed that euxanthic acid, which is combined with magnesia in the purree of commerce, can be decomposed by heating with hydrochloric acid, thus: C19H18010 +H2O = С1H2O1 + C6H10O; that is, two substances, euxanthone and an acid which was shown by Spiegel (Abstr., 1883, 219) to be glycuronic acid. From glycuronic acid a crystalline anhydride (CHO) can be obtained. From the glycuronic acid, obtained from purree, an anhydride with the same formula is also obtainable. melting point is 160°, when the heat is gradually applied; 170-180° when it is rapidly applied. Its specific rotation is (a)D = +19.4.


Euxanthone was obtained free from glycuronic acid by crystallising out the anhydride; it was obtained free from the remainder of the euxanthic acid by treating with ether in which euxanthone is readily solable. The statement of text-books that euxanthic acid is readily soluble in ether is an error. The separation may also be performed by treating with benzene.

A rabbit was fed on 0·7 gram of euxanthone; the urine was collected, evaporated to a small bulk, and hydrochloric acid added. After standing, a deposit of yellow needles was formed which were dissolved in alcohol and then recrystallised; they consisted of euxanthic acid. In order to settle the question whether purree is of animal or vegetable origin, urea, uric acid, and hippuric acid were sought for in it with positive results.

Purree is stated by some to be a deposit in the urine of camels if they eat the fruit of the Garcinia mangostana, from which Schmid separated the principle mangostin. When, however, rabbits are fed

upon the fruit or on mangostin, no euxanthic acid appears in the urine.

Schmiedeberg and Meyer regard the glycuronic acid as formed from the grape-sugar in the body. But if its formula, its optical properties, and its reduction power be considered, it is possible that it may have its origin in inosite. W. D. H.

Pyrrolidine. By A. LADENBURG (Ber., 20, 442-444).-Pyrrolidine is formed in small quantities during reduction of ethylene cyanide (Abstr., 1886, 528); the base is more conveniently prepared by the dry distillation of tetramethylenediamine hydrochloride. It boils at 85-88°, and fumes in the air when slightly warmed. The platinochloride forms orange-yellow crystals, and the bismuthoiodide, 3C,H,NHI,2Bila, red prisms. V. H. V.

Preparation of Pyridine Bases. By E. DÜRKOPF (Ber., 20, 444). -The aldehyde-ammonias, when heated with the aldehydes, yield bases of the pyridine series; thus collidine is formed from ethaldehyde and its ammonia compound. It appears probable that the ketones also undergo a similar change.

V. H. V.


Lutidines of Coal-tar. By G. LUNGE and J. ROSENBERG (Ber., 127-137). The sulphuric acid used in purifying coal-oil was diluted with 3 or 4 times the volume of water, left for several days and filtered. The filtrate was evaporated, treated with aqueous soda, and the oil so obtained separated and steam-distilled. It was then dried by means of caustic alkali and fractionally distilled. 20 litres of sulphuric acid yielded 800 grams of mixed bases. The fraction boiling at 141-144° yielded by precipitation with mercuric chloride (Ladenburg and Roth, Abstr., 1885, 557) the mercuriochloride of lutidine, from which the pure base was separated and identified. The fraction boiling at 153-156° yielded a-y-lutidine; this was converted by oxidation into a-lutidinic acid. When the fraction boiling below 170° was oxidised with potassium permanganate, a-lutidinic and isocinchomeronic acids were obtained. The formation of the latter acid points to the presence of a-B-lutidine in the mixed bases. The acid was separated by the method of Weidel and Herzig (Wien. Akad. Ber., 80, 821). N. H. M.

Ethoxylutidine. By F. CANZONERI and G. SPICA (Gazzetta, 16, 449-453).—When ethyl acetoacetate is heated with excess of ammoniacal zinc chloride in sealed tubes at 100-110°, an ethoxylutidine is formed along with other products, and a considerable quantity of carbonic anhydride is evolved; the reaction is as follows:2COMe CH, COOEt + NH, = C,NH2Me2OEt + CO2+ EtOH + 2H2O. This compound is a pale-yellow liquid boiling at 245-247°, and resembling pyridine in odour.

On repetition of former experiments (Abstr., 1885, 751) on the condensation of ethyl acetoacetate and formamide, an ethyl monolutidinecarboxylate was obtained as a transparent, yellow liquid of peculiar odour, boiling at 250-255°; this compound appears to be

isomeric with the ethyl monolutidinecarboxylate obtained by Michael from aldehyde, aldehyde ammonia, and ethyl acetoacetate (Abstr., 1885, 1244). V. H. V.

Action of Ammonia and of Primary Amines on Ethyl Dimethylpyronedicarboxylate. By M. CONRAD and M. GUTHZEIT (Ber., 20, 154-162).—Ethyl acetyllutidonecarboxylate,

[blocks in formation]

is obtained by heating ethyl lutidonecarboxylate (Abstr., 1886, 334) with an excess of acetic anhydride at 140-150°. It dissolves readily in ether and in boiling alcohol; it melts at 65°.

Lutidonecarboxylic acid, CO C(COOH): CMe

C(COOH): CMeNH, separates

from its aqueous solution in prisms which melt at 267° with evolution of carbonic anhydride. It is very sparingly soluble in hot water, alcohol, and ether. The calcium salt (with 2 mols. H2O) is readily soluble in hot water; the copper salt (with 14 mol. H2O) and other salts were prepared.

Lutidone (2, 6-dimethylpyridine), CO<CH: CMe



NH, is formed when the carboxylic acid is heated at 270-290° until no more carbonic anhydride is given off; it is best purified by distillation. It is very readily soluble in water and alcohol, almost insoluble in ether, benzene, and chloroform. It separates from the aqueous solution in lustrous, monoclinic needles (with 3 mols. H2O); a: b c = 1·1396: 1:2·6179; B = 85·11°. The anhydrous substance melts at 225° and boils at 349-351°. It gives a brown-red coloration with ferric chloride. It is identical with the compound obtained by Haitinger from dehydracetic acid (Abstr., 1885, 761). The platinochloride, (C,H,NO)2, H2PtCle, forms microscopic, transparent plates which melt at 224-225°. The chromate crystallises in well-formed, yellowish-red prisms, readily soluble in water, sparingly in alcohol. It melts at 125° with decomposition. The picrate crystallises in slender needles melting at 219-220°.

Ethyl methyllutidonedicarboxylate, CO (COOEt): CMNMe, is C(COOEt): CMeformed when solutions of ethyl dimethylpyronedicarboxylate and methylamine in acetic acid are mixed. It crystallises in rosettes of needles melting at 193°. The free acid melts at 255°, and at the same time decomposes into carbonic anhydride and methyllutidone. The latter crystallises in long, lustrous needles which melt at 110—111°; it dissolves readily in alcohol and water.


>NPh, is

Phenyllutidonedicarboxylic acid, COC(COOH): CMe prepared by the hydrolysis of the ethyl salt (Abstr., 1886, 334). It crystallises in prisms readily soluble in boiling alcohol, sparingly in ether, benzene, and water. The hydrogen barium salt, (C15H1NO,),Ba +H2O, is readily soluble; other salts were prepared.

Phenyllutidonemonocarboxylic acid, CMe NPh-CMe:

CH-CO-C-COOH, is obtained by heating the dicarboxylic acid at 227°. It crystallises in long, lustrous needles which melt at 257°; it dissolves in hot water and alcohol.


Phenylbutilone, CO<CH: CMe>NPh, is prepared by heating phenyllutidonedicarboxylic acid at 270°. It is identical with the compound obtained by Perkin from aniline and dehydracetic acid (Abstr., 1885, 762). N. H. M.

Lutidine-derivatives from Lutidinedicarboxylic Acid. By M. CONRAD and W. EPSTEIN (Ber., 20, 162–166).- When lutidone is distilled with zinc-dust, lutidine is formed. It boils at 144–145°, and is identical with that obtained by Epstein (Abstr., 1886, 257) from 2, 6-dimethylpyridinetricarboxylic acid. >N, is pre


pared by heating lutidonedicarboxylic acid with three times its weight of phosphorus pentachloride and some phosphorus oxychloride at 140°. The oxychloride is then mostly distilled off, the residue treated with water, filtered, and evaporated. It crystallises from water in white prisms which become brown at 217° and melt at 224°.

Chlorolutidinedicarborylic acid, CCC CMe

Chlorolutidine, C,NH,Cl, is obtained by heating dry lutidone (20 grams) with phosphoric chloride (35 grams), and some phosphorus oxychloride at 140°. It is purified by steam distilling. It is a clear colourless oil having an odour resembling that of lutidine; it boils at 178°; sp. gr. at 17° 1.105. The hydrochloride forms slender needles. The platinochloride and mercurichloride melt at 225° and 155° respectively. Chlorolutidine suspended in water gives with picric acid a yellow compound melting at 150--156°. The chromate forms orange-coloured crystals which blacken at 140°. Ethoxylutidine, obtained by heating chlorolutidine with alcoholic solution of sodium ethoxide, is a colourless oil boiling at 217°.

Phenylamidolutidine, C,NH,Me, NHPh [Me: NH: Me 2:4:6], is formed when chlorolutidine and aniline are heated at 195° for one hour. It melts at 150°, and boils at 335-338', and dissolves readily in alcohol, ether, and dilute acids. When treated with sulphuric acid, and then with a trace of nitric acid, it gives a blood-red coloration, which disappears on adding water or more nitric acid. The platinochloride forms slender needles which melt at 209°.

N. H. M.

Condensation Product of Ethyl Amidoacetoacetate with Hydrochloric Acid. By N. COLLIE (Ber., 20, 445-447).—In a former paper it has been shown that ethylic amidoacetate yields pyridine-derivatives on condensation (Abstr., 1885, 373). If hydrogen chloride is passed into an ethereal solution of this substance an additive compound, CHINO,,HCl, is produced, which forms deliquescent crystals, and is decomposed in aqueous solution into ethyl acetoacetate and ammonium chloride, but when heated by itself it


yields a substance, C10H1NO3, isomeric with the ethyl salt of a hydroxylutidinecarboxylic acid, melting at 137°, and showing remarkable stability towards reagents. On treatment with concentrated potash, and acidification of the product, an acid, C,H,NO3, is formed; this is an insoluble crystalline powder which melts at 300°, with evolution of carbonic anhydride and distillation of a white crystalline substance, C,H,NO, which melts at 176°, and boils without decomposition at 306.5°. From these properties, it is probably identical with pseudolutidinecarbostyril. In like manner ethyl amidoacetoacetate hydrochloride when heated with 1 mol. of the amido-acid itself yields ethyl pseudolutidostyrilcarboxylate, from which the carbostyril is obtained V. H. V.

by hydrolysis.

Ethyl Dimethylpyronedicarboxylate. By M. CONRAD and M. GUTHZEIT (Ber., 20, 151–154).-Ethyl 2, 6-dimethyl-3, 5-pyronedicarboxylate, C15H16O6 (Abstr., 1886, 333), melts at 80°. When 1 gram of the ether is boiled with aqueous baryta, acetone (0·08 gram), barium malonate (0·17 gram), and barium acetate are formed; no oxalate is produced. This decomposition corresponds with that of dehydracetic acid, which was shown by Oppenheim and Precht (Ber., 9, 323) to be decomposed by bases into acetone, acetic acid, and carbonic anhydride. Wislicenus (Ber. chem. Gesell. Würzburg, 17, 16) found that malonic acid is also formed in larger or smaller amount, in the decomposition of dehydracetic acid, according to the strength of the baryta solution. N. H. M.

Quinoline. By E. LELLMANN and H. ALT (Annalen, 237, 307327)-1, 4-Dimethylquinoline, C,NH,Me, prepared by the action of sulphuric acid on a mixture of paraxylidine sulphate, nitrobenzene, and glycerol. The product is poured into water, and the excess of nitrobenzene removed by distillation in a current of steam. The base is liberated by the addition of an alkali, and distilled in a current of steam. It is a liquid boiling at 265° under 736 mm. pressure. It solidifies in a freezing mixture, forming colourless crystals which melt between 4° and 5°. The sp. gr. of the liquid is 1070 at 21°. The dichromate, (CHN)2, H2Cr2Ö,, melts at 149°, and crystallises in orange-coloured needles. The platinochloride forms anhydrous needles. When oxidised with nitric acid (22 per cent.) at 170°, the base is converted into 1, 4-methylquinolinecarboxylic acid, C,NH,Me-COOH. This acid melts at 286°. The hydrochloride, CH,O2N,HCl + H2O, forms silky needles, which are decomposed by water. The platinochloride contains 6 mols. H2O.

The ammonium salt gives a crystalline precipitate with calcium chloride, and amorphous precipitates with ferrous sulphate, lead acetate, and copper salts. The methylquinoline which is produced when this acid is heated with lime is identical with the methylquinoline from orthotoluidine.

1, 4-Bromoquinolinecarboxylic acid, C,NH,Br-COOH, is prepared by heating at 160° a mixture of parabromometamidobenzoic acid, orthonitrophenol, glycerol, and sulphuric acid. The product is mixed with water, and the excess of nitrophenol distilled off in a current of steam.

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