Some derivatives of 4 (or 5)-methylglyoxaline / by A.J. Ewins.

  • Ewins, Arthur James.
Date:
1910
Catalogue details

Licence: In copyright

Credit: Some derivatives of 4 (or 5)-methylglyoxaline / by A.J. Ewins. Source: Wellcome Collection.

Provider: This material has been provided by The Royal College of Surgeons of England. The original may be consulted at The Royal College of Surgeons of England.

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    Experimental. Interaction of 4(or 5')-Methylylyoxalinc and Formaldehyde. Five grams of 4(or 5)-metliyIglyoxaIine were heated in a sealed tube for two hours at 120° with 10 c.c. of a 40 per cent, solution of formaldehyde. There was no pressure on opening the tube, and to the clear, light yellow contents was added a hot saturated aqueoti- solution of G-5 grams of picric acid. On cooling, a yellow, crystalline solid separated, which after recrystallisation from dilute (50 per- cent.) alcohol was obtained quite pure. Yield, 9 grams. 4(or 5)-Methyl-5(or A)-hydroxymethylylyoxaline, ch3-c.nh HO-CHs-C— The free base was obtained from the picrate by converting the latter into the hydrochloride, and treating the solution so obtained with excess of sodium carbonate. The alkaline solution was evapor- ated to dryness, the residue extracted with absolute alcohol, and the solution concentrated. On keeping, the crystalline base slowly separated in stout, hexagonal prisms, melting at 138°: 0 1568 gave 0-3074 C02 and 0-1002 H20. C = 53'5; H = 7T. 03084 „ 682 c.c. N2 (moist) at 23° and 758 mm. N = 25'2. C5HsON2 requires C = 536; H = 7T; N = 25’0 per cent. The base is very readily soluble in water or alcohol, but sparingly so in most other organic solvents. Solutions of the base or of its salts give an intense cherry-red coloration with p-diazobenzenesul- phonic acid. In neutral or alkaline solution it gives a precipitate with mercuric chloride, which is soluble in dilute acid. With jihosphotungstic acid solution it gives a precipitate, which is readily soluble in hot water or cold acetone, and may readily be crystallised from dilute acetone, forming fan-shaped clusters of short, broad prisms. The hydrochloride, obtained from the picrate in the usual manner, crystallises from absolute alcohol, the yield being increased by addition of a little dry ether. It forms stout, hexagonal plates, melting at 240—242°. The salt is deliquescent, and readily soluble in water or alcohol: 0-1658 gave 0-2440 C02 and 0'0892 H20. C=40*l; H = 5'9. 0T340 „ 22‘4 c.c. N2 (moist) at 23° and 758 mm. N = 190. 0-1580 „ 0-1524 AgCl. Cl = 23-8. CsHgON^HCl requires C = 403; H = 6 0; N = 188j Cl = 240 per cent.