6-alkoxy-7-hydroxyquinoline-3-carboxylic acids and...

C - Chemistry – Metallurgy – 07 – D

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260/288, 260/289

C07D 215/26 (2006.01) C07D 215/56 (2006.01)

Patent

CA 1044239

ABSTRACT This invention relates to a process for the preparation of the com- pounds of the general formula I: Image (I) wherein R1 stands for lower alkyl group, R2 stands for a lower alkyl group or an aralkyl group, R3 stands for hydrogen or a lower acyl group which comprises (a) reducing a compound of the general formula II: Image (II) wherein R1 and R3 are defined above, to a compound of the general formula III: Image (III) and reacting the compound thus obtained with an ethoxy-methylene-malonic acid- diester of the general formula IV: Image (IV) wherein R2 is defined above and subjecting the compound of the general formula V: Image (V) thus obtained, wherein R1, R2 and R3 are defined above, to ring-closure; or (b) reacting a compound of the general formula: Image (VI) wherein R1 and R3 are defined above, with ortho-formic acid ester and alkyl- malonate and subjecting the compound of the general formula V thus obtained, wherein R1, R2 and R3 are defined above, to ring-closure; or (c) subjecting a compound of the general formula I, wherein R1 and R2 are defined above and R3 stands for a lower acyl group, to a selective acyl-cleaving; or (d) reacting the compound of the general formula III, wherein R1 is defined above and R3 stands for hydrogen, with ethyl-.alpha.-cyano-.beta.-ethoxy-acrylate and subjecting the compound of the general formula VII: Image (VII) thus obtained, wherein R1 is defined above, to ring-closure and subjecting the new compound of the general formula VIII: Image (VIII) wherein R1 is defined above, to acidic or alkaline hydrolysis and subsequently to esterification; or (c) reacting a compound of the general formula VIII with an alcohol in an acidic medium: or (f) converting a compound of the general formula I, wherein R3 stands for hydrogen, into an acid and forming an ester of the general formula I from the acid by reacting with the corresponding alcohol and converting the compound thus obtained into a salt or setting free the compound from the salts thereof. It also elates to the new compounds of formula I which are useful as coccidiostatic and as intermediates in the synthesis of the known coccidiostatic-6,7-dialdoxyquinoline carboxylic acid esters. Other new intermediates are described.

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