The action of nitric acid on the ethers of aromatic hydroxyaldehydes / by Arthur H. Salway.

  • Salway, Arthur H. (Arthur Henry)
Date:
[1909?]
Catalogue details

Licence: In copyright

Credit: The action of nitric acid on the ethers of aromatic hydroxyaldehydes / by Arthur H. Salway. Source: Wellcome Collection.

    10/16 (page 1162)
    5-Amino-l-methoxy-2 : 3-metliylenedioxybenzene y CH2<C| 0 0 NHf OMe (а) Preparation from Myristicinamide.—Finely powdered myristi- cinamide was shaken continuously for several hours with the theoretical quantity of a freshly-prepared solution of sodium hypo¬ chlorite (compare Graebe, Ber., 1902, 35, 2753), and the mixture finally heated at 100° for a short time. The product was then cooled and extracted with ether, when the ethereal solution, after evaporation, yielded an oily residue, which soon solidified. It was purified by crystallisation from water, from which it separated in colourless leaflets, melting at 85—86° : 0T076 gave 0-2263 C02 and 0*0553 H20. C = 57*4 ; II = 5-7. C8H903N requires 0 = 57*5; H = 5*4. (б) Preparation from 5-JVitro-l-methoxy-2 : 3-methylenedioxybenzene. —To 1 part of the finely divided nitro-compound 5 parts of stannous chloride in 15 parts of concentrated hydrochloric acid were added, and the mixture was gently warmed for one hour. A crystalline tin double salt of the amino-compound was formed, from which the tin was removed by means of hydrogen sulphide. The aqueous solution was then concentrated to a small bulk, rendered alkaline with sodium carbonate, and extracted with ether; the ethereal solution, after evaporation, left a residue which rapidly solidified and was crystal¬ lised from hot water, when it was deposited in colourless leaflets melting at 85—86°. When this substance was mixed with the 5-amino- 1-methoxy-2 :3-methylenedioxybenzene, prepared from myristicin¬ amide as above described, the melting point remained unchanged. Further confirmation of the identity of the two products was obtained by the preparation from each of the same benzoyl derivative, melting at 128—129°. 5-Amino-l-methoxy-2 : 3-methylenedioxybenzene is readily soluble in benzene, ether, chloroform, ethyl acetate, or alcohol, but only sparingly soluble in light petroleum. It is best crystallised from hot water, but can also be crystallised from a mixture of benzene or alcohol and petroleum. Its hydrochloride crystallises from dilute alcohol in well-formed, colourless needles, which decompose at about 245°. It yields a benzoyl derivative, which crystallises from alcohol in colourless rosettes of feathery needles melting at 128—129° : 0-1136 gave 0*2770 C02 and 0*0506 H20. 0 = 66*5 ; H = 4*9. C15Hi304N requires 0 = 66*4; 11 = 4*8 per cent.