Ciba-geigy Corporation

Peter Labuhn

Ernst Aufderhaar

Alfred Grieder

Jean-Jacques Gallay

Klaus-Jurgen Coers

A process is described for the preparation of N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the formula ##STR1## in which R.sub.1 and R.sub.2 are each methyl or ethyl and R.sub.3 is an alkyl group having 1 to 4 carbon atoms, this process being based on the reaction of a corresponding 2,6-dialkylaniline with a corresponding alkyl 2-chloropropionate or alkyl 2-bromopropionate. The process is carried out by carrying out the reaction of the 2,6-dialkylaniline with the 2-halogenopropionic acid ester at 110.degree.-130.degree. C. in the presence of an alkali metal iodide as the catalyst, and of an alkali metal carbonate or alkali metal bicarbonate as an acid acceptor, in excess 2,6-dialkylaniline as the solvent, removing, by distillation, the water formed during the reaction and working up the organic phase, which is obtained after adding water and separating the phases, by distillation. The N-(1'-alkoxycarbonylethyl)-2,6-dialkylanilines of the above formula which can be prepared by this process are valuable intermediates for the preparation of compounds having a pesticidal action.

Process for the preparation of

A new process for the production of 3,4-dialkoxyanilines in which the two alkyl groups are different from each other is disclosed. The process comprises the stepwise introduction of the alkyl groups in different stages of the process by converting pyrocatechol into its monoalkyl ether, coupling said monoalkyl ether with a phenyldiazonium salt, alkylating the 3-alkoxy-4-hydroxy-azobenzene obtained to form 3,4-dialkoxyazobenzene and reductively cleaving the latter to the corresponding 3,4-dialkoxyaniline. The 3,4-dialkoxyanilines obtainable by the new process are valuable intermediates for the preparation of 4-hydroxy-6,7-dialkoxy-3-quinoline carboxylic acid esters which are excellent coccidiostats.

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Birsfelden, Switzerland

Peter Labuhn