GB809286A - Basically substituted butyric acid anilides and process for their manufacture - Google Patents

Abstract

The invention comprises compounds of the general formula <FORM:0809286/IV (b)/1> in which R1 is hydrogen or an alkyl or alkoxy group of 1-4 carbon atoms, and is preferably a para-alkoxy group of 1 to 3 carbon atoms, and R2 is hydrogen or an alkyl group, and acid addition salts of these compounds. The compounds are made by reacting an acetoacetic acid anilide with ammonia or a primary alkylamine and a reducing agent and if desired subjecting the product to alkylation. Suitable acetoacetic acid anilides include the acetoacetyl derivatives of p-anisidine, p-phenetidine, p-toluidine and p-ethyl aniline, and the corresponding o- and m-derivatives. Suitable amines include methylamine, ethylamine, isopropylamine, butylamine and isobutylamine. The reaction may be carried out in a single stage or in two stages with isolation of the intermediate aminocrotonic acid anilide. The reduction is suitably effected by nascent hydrogen, aluminium or sodium amalgam in alcohol, lithium aluminium hydride, sodium boron hydride, electrolytic reduction or catalytic hydrogenation, preferably in solution in a solvent such as methanol or ethanol. The basic anilides may be converted into their salts with for example formic, acetic, malonic, maleic, succinic, lactic, malic, tartaric, citric, hydroxyethane sulphonic, aceturic, 1-phenyl-2 : 3 - dimethyl - pyrazolone - (5) - 4 - methylaminomethane sulphonic, ethylenediaminetetracetic, benzoic and salicyclic acids. Examples describe the preparation of b -n-butylamino-butyric acid-p-phenetidide, b -n-butylamino-butyric acid anilide, methylamino-butyric acid-p-phenetidide and b -amino-butyric acid-p-phenetidide, and the isolation of these compounds as free bases or acid addition salts. Butylamino-crotonic acid para-phenetidide is obtained as an intermediate by the reaction of acetoacetic acid p-phenetidide with n-butylamine.