Syntheses in the epinephrine series / by Frank Tutin, Frederic W. Caton and Archie C.O. Hann.

  • Tutin, Frank.
Date:
[1909?]
Catalogue details

Licence: In copyright

Credit: Syntheses in the epinephrine series / by Frank Tutin, Frederic W. Caton and Archie C.O. Hann. Source: Wellcome Collection.

    13/18 page 2123
    0*1760 in 19'5 of benzene gave M — 0*125°. M.W. =410. 0'1098 „ 22*2 „ naphthalene gave — 0'080°. M.W. = 426. C24H2608 requires M.W. =442. a-p-Hydroxyphenylethylamine. Eight grams of p-hydroxyacetophenoneoxime (m. p. 144—145°) were dissolved in 100 c.c. of aqueous methyl alcohol, and twice the theoretical amount of 2 per cent, sodium amalgam gradually intro¬ duced in small pieces, the mixture being constantly maintained acid by the frequent addition of acetic acid. When all reaction had ceased, the liquid was extracted with ether to remove un¬ changed oxime, after which it was rendered alkaline by means of potassium carbonate, and repeatedly extracted with amyl alcohol. The resulting amyl-alcoholic liquids were ext?acted with successive quantities of dilute hydrochloric acid, and the combined acid liquids concentrated under diminished pressure. a-p-Hydroxy- phenylethylamine hydrochloride then separated in stout prisms, which were purified by recrystallisation from water. This salt is soluble in alcohol, and insoluble in ethyl acetate; it possesses no definite melting point, but gradually softens, and darkens at 200—280°. Above the latter temperature it yields a sublimate of ammonium chloride, together with phenol, but it was ascertained that no p-vinylphenol was formed : 0-1527 gave 0*3086 C02 and 0*0964 H20. C = 55T ; H = 7*0. C8H120NC1 requires C = 55'4; 11 = 6*9 per cent. a-p-Hydroxy phenyl ethyl amine, as obtained from its hydrochloride, was sparingly soluble in water or alcohol, and insoluble in ether or chloroform. It formed an amorphous, gum-like mass, which could not be crystallised. The dibenzoyl derivative, prepared by the Schotten-Baumann method, crystallises from dilute alcohol in fine needles, and melts at 187—188°: 0T528 gave 0*4280 C02 and 0*0758 H20. C = 76*4; H = 5*5. C^H^OgN requires C = 76*5; H=5*5 per cent. a-p-Hydroxy-^-benzoylphenylethylamine, HO*C6H4*CHMe*NHBz, was formed on heating the dibenzoyl derivative with 5 per cent, alcoholic potash. It crystallises from alcohol in large, hexagonal prisms, melting at 156°: 0*1125 gave 0*3096 C02 and 0*0631 H20. C = 75*0; H = 6*2. C15H1502N requires C = 74'8; 11 = 6*2 per cent. Several attempts were made to prepare a-2?-dihydroxy-a-phenyl- ethane by the action of heat on the nitrite of a-p-hydroxyphenyl- •ethylamine, but the products so obtained were very unstable in the
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