Verfahren zur Herstellung von 3,4-Dihydro-benzoxazinonen-(1,3,2)

3,4 - Dihydro - benzoxazinones - (1,3,2) of the formula wherein R represents a hydrogen atom or a methyl or ethyl group and wherein the aromatic ring may carry one or more chlorine, bromine, methyl and/or nitro substituents, are prepared by reacting the corresponding unsubstituted or substituted o-...

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Hauptverfasser: GAMS,ERWIN,DR, SCHULTE,KARL,DR, THESING,JAN, SOMMER,SIEGMUND,DR
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SCHULTE,KARL,DR
THESING,JAN
SOMMER,SIEGMUND,DR
description 3,4 - Dihydro - benzoxazinones - (1,3,2) of the formula wherein R represents a hydrogen atom or a methyl or ethyl group and wherein the aromatic ring may carry one or more chlorine, bromine, methyl and/or nitro substituents, are prepared by reacting the corresponding unsubstituted or substituted o-hydroxy-benzyl-amines of the formula with phosgene. The reaction is preferably carried out in an inert organic solvent, e.g. benzene, toluene, ether or dioxan, and with the addition of a base, e.g. pyridine, triethylamine or dimethylaniline. It is also possible to work in an aqueous medium, e.g. in aqueous sodium hydroxide. The reaction mixture is cooled at the beginning of the reaction, preferably to a temperature between - 10 DEG and + 15 DEG C., and the reaction is ended by allowing the mixture to stand at room temperature or by heating or boiling under reflux. o - Hydroxy - benzylamines of Formula II may be prepared by reducing the oximes of the corresponding o - hydroxybenzaldehydes or methyl or ethyl o-hydroxyphenyl ketones, or by reacting the corresponding o-hydroxybenzyl halides with hexamethylene tetramine and subsequently decomposing the salts obtained with an acid.
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