A new synthesis of 4(or 5)-L-aminoethylglyoxaline, one of the active principles of ergot / by Frank Lee Pyman.

  • Pyman, Frank Lee.
Date:
[between 1910 and 1919?]
Catalogue details

Licence: In copyright

Credit: A new synthesis of 4(or 5)-L-aminoethylglyoxaline, one of the active principles of ergot / by Frank Lee Pyman. Source: Wellcome Collection.

    11/16 (page 678)
    alkaline with 80 c.c. of 10 per cent, aqueous sodium carbonate, and evaporated to dryness under diminished pressure. The residue was thoroughly extracted with ether, and gave 5*6 grams of pale yellow oil; this was mixed with its own weight of oxalic acid, and the acid oxalates fractionally crystallised from water, when 3*4 grams of pure 4(or b)-ethoxymethylglyoxaline hydrogen oxalate were obtained; besides this oxalate, which separates first in large crystals, other crystalline oxalates were present in the mother liquors. No 4(or 5)-cyanomethylglyoxaline hydrogen oxalate could be isolated from them by fractional crystallisation, and they were not further examined. 4(or h)-Ethoxymethylglyoxalinc, CH’NHn C2H5*0-CH2-0-' This base is liberated from the oxalate by treating the latter with baryta, filtering from barium oxalate, and removing the excess of baryta as carbonate. It crystallises from anhydrous ether in prismatic needles, which sinter from 50°, and melt at 53—4)5° (corr.). It is easily soluble in water, and the usual organic solvents, with the exception of light petroleum: 0*1530 gave 0*3219 C02 and 0*1097 H20. C = 57*4; H = 8*0. 0*1533 „ 0*3199 C02 „ 0*1094 H20. C = 56*9; H = 8*0. C6H10ON2 requires C = 57*l; TI = 8*0 per cent. The hydrogen oxalate crystallises from water in large prisms, which melt at 165—167° (corr.). It is anhydrous, and is soluble in about 4 parts of cold water, but readily so in hot water: 0*1563 gave 0*2668 C02 and 0*0839 H20. 0 = 46*6; H = 6*0. 0*1443 „ 0*2457 C02 „ 0*0794 H20. C = 46*4 ; H = 6*2. 0*1274 „ 16*0 c.c. N2 at 21° and 754 mm. N = 14*5. ^C6H10ON2)4,(C2H2O4)3 requires 0 = 46*5; H = 6*0; N = 14*6 per cent. The Reduction of 4(or b)-Cyanomethylglyoxaline. Preparation of 4 (or 5)-fi-Aminoethylglyoxaline. Ten grams of 4(or 5)-cyanomethylglyoxaline were dissolved in 50 c.c. of absolute alcohol, and 25 grams of sodium added piece by piece within a few minutes. Further quantities of hot absolute alcohol were added a few c.c. at a time, while the mixture was heated by a small flame, until after the addition of about 200 c.c. of absolute alcohol (making 250 c.c. in all) in the course of an hour and a-quarter, nearly all the sodium had dissolved. A little