The electrolytic reduction of pheno- and naphtho-morpholones / by Frederic H. Lees and Frank Shedden.

  • Lees, F. H. (Frederic Herbert)
Date:
[1903.]
Catalogue details

Licence: In copyright

Credit: The electrolytic reduction of pheno- and naphtho-morpholones / by Frederic H. Lees and Frank Shedden. Source: Wellcome Collection.

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    enolic modification of acetyl-o-aminophenol. Its formation might be explained by assuming that phenomorpholone exists in solution as mixture of its tautomeric isomerides, which respectively suffer disruption during reduction in the manner already shown, giving rise to the two corresponding isomeric acetyl aminophenols. , assuming that the rate of formation of the immo-form of acetyl- o-aminophenol exceeds that of its transformation into the amino- modification, it is only necessary that the contents of the elec^’^ cell should be diluted at an appropriate stage in order to cause the separation of the less basic isomeride. . . According to the formula suggested, isoacetyl-o-aminophenol the hydroxy-derivative of an iV-arylacetiminoether, and is the first examp e of this class of compound. The following scheme possibly represents the reduction of phenomorpholone : .0—CH, C6H4<^H-CO ,0K CH, C6H4<nh.co I A 4 C6H4< .0-ch2 •NiC-OH + 2H -7* If c6h4<ot^ + 4H .OH CH, —> C6H4<NH-6h, —C*OH On electrolytic reduction, iY-methylphenomorpholone also, for themost part underwent disruption in the same way, and gave as the principal products V-acetylmethyl-o-aminophenol and Mhylethyl-o-am^nophenoL Tn this case however, a yield of about 10 per cent, of A-methylpheno- morpholine was obtained, this product being identical in all respects with that prepared by Knorr by another method (Ber., 1889, 22, Attempts^o^prepare^^morpholone from a-naphthol according to the method which so readily gives phenomorpholone were without success, • to the very sparing solubility in water of the sodium potassium derivatives of /3-nitro-a-naphthol, which renders their inter¬ action with sodium chloroacetate impracticable, the latter becomi g l oQf entirely hydrolysed before the desired condensation h sary /3-nitro-a-naphthoxyacetic acid by another method, name y, y nitrating a-naphthoxyacetic acid, was also unsuccessful, as the resu nitro-acid did not yield a morpholone on reduction, an w«f the a-nitro-acid, the nitration having taken place as m ^ a-naphthyl ethyl ether (compare Heermann, J. pr. Che » 240n the other hand, a-nitro-^naphthoxyacetic acid was thft either by nitrating /3-naphthoxyacetic acid, or by ° Qn :Sl salt of a-nitro-/3 naphthol with sodium chloroacetate. On.