Imperial Chemical Industries Limited

Alan Cyril Tucker

Albert Edward Kaye

Ronald James Hurlock

Compounds of formula: ##STR1## wherein both groups X are chlorine, bromine or trifluoromethyl, or one X is chlorine or bromine and the other is trifluoromethyl, and Y is --CN or --COOR in which R is an alkyl group, are obtained by (A) reacting a compound of the formula: ##STR2## wherein X.sup.1 is chlorine or bromine, with a compound of the formula:

Process for the preparation of cyclopropane derivatives, intermediates

A process for the manufacture of 2-cyano-propionate esters which comprises hydrogenating in the presence of an hydrogenating catalyst a mixture of a cyano-acetic ester, formaldehyde and a condensation catalyst. Typically ethyl cyano-acetate is treated with formalin or paraform and hydrogen in the presence of palladium on carbon and zinc acetate. Preferably an antioxidant or polymerisation inhibitor is also included in the reaction mixture which also usually includes solvents such as glacial acetic acid or toluene.

Manufacture of 2-cyano-propionate esters

Reaction of a 2-amino-, 2-alkylamino- or 2-dialkylamino-4-hydroxypyrimidine, preferably also containing a methyl group at the 6 position, with an aldehyde R--CHO in presence of hydrogen and a hydrogenation catalyst introduces an alkyl group R--CH.sub.2 -- into the 5 position. The reaction is preferably carried out under superatmospheric pressure at a temperature between 80.degree. and 180.degree.C and is aided by metal salts, acids, amines, amine salts or basic ion-exchange resins.

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Alan Cyril Tucker