Process for the production of alpha-ketocarboxylic acid amides a

Details Process for the production of alpha-ketocarboxylic acid amides a Process for the production of alpha-ketocarboxylic acid amides a

1977-06-02

1979-07-17

Waltz, Thomas

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260404, 260561K, C07C10202, C07C10208, C07C10319, C07C103127

Patent

active

041614917

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.

REFERENCES:
patent: 2434507 (1948-01-01), Mostek
Birchall et al., Cun. J. Chem. 49, 919 (1971)-Abstract.
Oakwood et al., Org. Synth. 24, 16 (1944)-Abstract.
Claisen et al., Berichte 13, 2121 (1880).
Moritz, J. Chem. Soc. (London) 39, 13-19 (1881).
Patai, ed., The Chemistry of Amides, pp. 120-121, (1970).

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