Accession Number : AD0616801

Title :   OXIMES. I. THE SYNTHESIS OF SOME SUBSTITUTED 2-OXIMINOACETOPHENONES,

Corporate Author : DEFENCE CHEMICAL BIOLOGICAL AND RADIATION LABS OTTAWA (ONTARIO)

Personal Author(s) : Norman,J. J. ; Heggie,R. M. ; Larose,J. B.

Report Date : 16 MAR 1962

Pagination or Media Count : 8

Abstract : The preparation of some p-(omega-dimethylaminoalkyl)- and p(omega-dimethylaminoalkoxy)-2oximinoacetophenones and their methiodides is described. No general method was found for synthesis of shortchain (Co, C1, C2) p-(omega-dimethylaminoalkyl)-2oximinoacetophenones. The longer-chain compounds (C3, C4) were prepared by a method which would appear to be general. Omega-Phenyl-1-haloalkanes undergo Friedel-Crafts acylation to yield p-(omega-haloalkyl)acetophenones. These were converted to the dimethylamino compounds, which, subsequently, yielded 2oximinoacetophenones. No method of preparation of p-(2'-dimethylaminoethyl)-2-oximinoacetophenone was found. Synthesis of p-(omega-dimethylaminoalkoxy)-2oximinoacetophenones was accomplished using mixed alpha,omega-dihaloalkanes and p-hydroxyacetophenone. The p-(omega-haloalkoxy)-acetophenones from these reactants were first converted to oximes and then to the dimethylamino compounds. Syntheses of p-(omegadimethylamino-ethoxy, -propoxy, -butoxy, and -pentoxy)2-oximinoacetophenones were achieved. That of p(dimethylaminomethoxy)-2-oximinoacetophenone was unsuccessful. (Author)

Descriptors :   (*OXIMES, SYNTHESIS(CHEMISTRY)), (*KETONES, SYNTHESIS(CHEMISTRY)), ORGANIC OXYGEN COMPOUNDS, IODIDES, AMINES, FRIEDEL CRAFTS REACTIONS, CHOLINESTERASE, PHENOLS, CANADA

Distribution Statement : APPROVED FOR PUBLIC RELEASE