(A) Creatinine.—A mixture of 900 g. (6 moles) of commercial creatine hydrate (Note 1) with 550 cc. of concentrated hydrochloric acid (sp. gr. 1.19) and 150 cc. of water is warmed in a 3-l. flask on the steam bath for twenty-four hours (Note 2). The hot solution is filtered and chilled to 0–5° in an ice bath, and to it is added 1 l. of 28 per cent aqueous ammonia (sp. gr. 0.90). The flask is immersed in an ice-salt bath, and the mixture is stirred vigorously until the temperature falls to 0°, when the crystalline creatinine is filtered off, washed with ice-cold 28 per cent aqueous ammonia (Note 3) until the filtrate is free of chlorides, and finally with ice-cold methyl alcohol; the product (Note 4) is then dried to constant weight at 40–50°. The yield (Note 5) is 545–555 g. (80–81 per cent of the theoretical amount).

(B) Creatinine Zinc Chloride.—An intimate mixture of 400 g. (2.7 moles) of commercial creatine hydrate and 400 g. (2.9 moles) of fused zinc chloride is heated in a porcelain dish over a small flame. The mixture melts to a viscous liquid which soon solidifies. The flame is removed when the mixture can no longer be stirred. The mass, when cold, is broken up, and stirred with 500 cc. of cold water until the lumps are softened; the crude creatinine zinc chloride is filtered off with suction on a hardened filter paper and washed with ice water to remove excess zinc chloride. The crude material is now dissolved in 6 l. of boiling 25 per cent aqueous acetic acid, filtered with the use of a little decolorizing carbon, and the solution allowed to stand for forty-eight hours. The crystals that have separated are filtered off, washed with ice water, and dried. The weight is 220–230 g. The filtrate and washings are evaporated to 4.5 l. under reduced pressure in a 12-l. flask; 6.5 l. of methyl alcohol is added and the mixture allowed to stand in a cool place for twenty-four hours. The crystals that separate are filtered off, washed with cold water and dried, and an additional 150–160 g. is thus obtained. The total yield is 370–380 g. (76–78 per cent of the theoretical amount).

(C) Creatinine Picrate.—A mixture of 300 g. (2 moles) of commercial creatine hydrate with 190 cc. of concentrated hydrochloric acid (sp. gr. 1.19) and 50 cc. of water is warmed in a glass or porcelain dish on a steam bath for twenty-four hours. The resulting mass of creatinine hydrochloride crystals is dissolved in 1 l. of water, boiled with a little decolorizing carbon, and filtered. The solution is then diluted to 4 l. with distilled water, and heated to boiling in a 12-l. flask under a reflux condenser. To the hot solution is added, with good stirring, a solution of 500 g. (2 moles) of technical picric acid (containing 10 per cent of water) in 1250 cc. of warm methyl alcohol. Stirring is continued for one hour on the steam bath and the solution allowed to cool. The crystalline precipitate of creatinine picrate is filtered off, washed well with cold water, and dried. It forms long needles which melt at 220°; the melting point (Note 6) is unchanged on recrystallization from hot water. The yield is 620–630 g. (89–90 per cent of the theoretical amount).