Production of .beta.-amino-.alpha.,.beta.-unsaturated carboxylic acid esters
AssigneeCiba-Geigy Corporation
InventorsLuigi Cassar, Abul Iqbal, Alain C. Rochat
Life of this patent
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Abstract
A process for producing a compound of the formula ##STR1## wherein A is aryl or alkyl, R.sub.1 is an aromatic radical and R.sub.2 is hydrogen, alkyl, aryl, cyano, --COOalkyl or --COOaryl, which process comprises reacting 1 mol of an aromatic nitrile of the formula R.sub.1 --CN (II) with 1 mol of an acetic ester of the formula (X)(R.sub.2)CH--COOA (III) in which X is halogen, in the presence of zinc, in an inert organic solvent and at a temperature of less than 80.degree. C.; hydrolyzing in an alkaline medium the formed reaction product; and then isolating the compound of the formula I. The compounds of the formula I are valuable intermediates for producing heterocyclic compounds.
Claims10
An improved process for producing a compound of the formula ##STR15## wherein A is alkyl of 1 to 12 carbon atoms, phenyl or phenyl substituted by chlorine, by alkyl of 1 to 6 carbon atoms or by alkoxy of 1 to 6 carbon atoms,
- R.sub.2 is hydrogen, alkyl of 1 to 12 carbon atoms, phenyl, phenyl substituted by chlorine, by alkyl of 1 to 6 carbon atoms or by alkoxy of 1 to 6 carbon atoms;
- cyano or the group --COOZ where Z is alkyl of 1 to 12 carbon atoms, phenyl or phenyl substituted by chlorine, by alkyl of 1 to 6 carbon atoms or by alkoxy of 1 to 6 carbon atoms, and
- R.sub.1 is phenyl or said phenyl substituted by one or two fluorine, chlorine or bromine atoms or mixtures thereof, by one, two or three methoxy or methyl groups or mixtures thereof with chlorine atoms, by cyano, by amino, by dimethylamino, by hydroxyl, by trifluoromethyl, by alkoxycarbonyl of 2 to 3 carbon atoms, by tert-butyl, by cyanophenyl, by acetyl or by alkylbenzoyloxy of 11-14 carbon atoms;
- biphenylyl;
- naphthyl or said naphthyl substituted by methoxy or by amino;
- anthryl;
- phenanthryl;
- pyrazolyl or said pyrazolyl substituted by amino;
- pyridyl or said pyridyl substituted by methyl, hydroxy or by amyloxy;
- indolyl;
- quinolyl;
- furyl or thienyl, by reacting equimolar amounts of a nitrile of formula II
- R.sub.1 CN (II)
- with an ester of formula III ##STR16## wherein X is halogen, in the presence of zinc, in an inert organic solvent at a temperature of less than 80.degree. C.,
- the improvement comprising
- hydrolyzing, the reaction product formed, in an alkaline medium;
- and
- isolating the compound of formula I.
Dependencies are inferred from the claim text.