Process for the production of alpha-ketocarboxylic acid amides and cycloaliphatic products

US4161491A · kind A · utility

Assignee

• Deutsche Gold- und Silber-Scheideanstalt Vormals Roessler

Inventors

• Axel Kleemann · Hanau, DE
• Herbert Klenk · Hanau, DE
• Werner Schwarze · Frankfurt, DE

Key dates

• Filing date: Jun 2, 1977
• Grant date: Jul 17, 1979
• Expiry date: Jun 2, 1997

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07C255/19
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

There are prepared .alpha.-ketocarboxylic acid amides of the formula ##STR1## where R is hydrogen, R.sub.1 and R.sub.2 are the same or different, R.sub.1 is alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms, and R.sub.2 is hydrogen, alkyl of 1 to 18 carbon atoms or haloalkyl, preferably chloroalkyl, of 1 to 18 carbon atoms or ##STR2## together is a cycloalkyl group of 3 to 8 carbon atoms which can be substituted by one or more 1 to 5 carbon atom alkyl groups or by one or more halogen atoms, preferably chlorine atoms, with the proviso that when ##STR3## form a cycloalkyl group then R can also be alkyl of 1 to 5 carbon atoms. The process comprises saponifying an acyl cyanide of the formula ##STR4## in which R, R.sub.1 and R.sub.2 are as defined above in an organic solvent or mixture of such solvents which is liquid and inert under the reaction conditions, first with gaseous hydrogen chloride and then treating with water at a temperature of about -70.degree. C. to about +70.degree. C. and then isolating the .alpha.-ketocarboxylic acid amide in conventional manner. Several of the cyclic .alpha.-ketocarboxylic acid amides are new compounds.