Improved methods of preparing 4-cyano-4-(substituted...

C - Chemistry – Metallurgy – 07 – D

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C07D 231/56 (2006.01) C07C 251/80 (2006.01) C07C 251/86 (2006.01)

Patent

CA 2252344

ABSTRACT An improved process for preparing a compound of Formula (1): Image comprising: (a) treating a compound of Formula (la): Image with an alcohol comprising a compound of Formula (Ib-A) and an acid comprising acompound of Formula (Ib-B): Ra-OH and HX (lb-A) (lb-B) wherein R. is selected from the group consisting essentially of hydrogen; (C1-C6) alkyl; phenyl and (C1-C3) alkyl-phenyl wherein said phenyl groups are optionally substituted by one or two substituents selected from the group consisting essentially of -(C1-C4) alkyl; -O(C1-C3) alkyl; Br; and Cl; and HX is an acid selected from the group consisting essentially of hydrobromic acid; hydrochloric acid; sulfuric acid; sulfonic acid; and aliphatic and aromatic sulfonic acids selected from the group consisting essentially of methanesulfonic acid, trifuoromethanesulfonic acid, benzenesulfonic acid, benzylsulfonic acid, p-toluene sulfonic acid, and camphorsulfonic acid, whereby HX provides the acidic conditions which result in formation of a salt of the corresponding imidate of Formula (lc): Image and (b) hydrolyzing said compound of Formula (lc) to provide said compound of Formula (1).

Méthode améliorée pour préparer un composé de formule (1) Image , consistant à : a) traiter un composé de formule (la) Image avec un alcool comprenant un composé de formule (Ib-A) et un acide comprenant un composé de formule (Ib-B), soit Ra-OH (Ib-A) et HX (lb-B), où R est choisi principalement parmi un hydrogène et un groupe alkyle C1-C6, phényle ou alkyl(C1-C3)phényle, lesdits groupes phényle étant facultativement avec substitution par un ou deux substituants choisis principalement parmi un groupe alkyle C1-C4, O-alkyle C1-C3, Br et Cl; HX est un acide choisi principalement parmi l'acide bromhydrique, l'acide chlorhydrique, l'acide sulfurique, l'acide sulfonique, et des acides sulfoniques, aliphatiques ou aromatiques, eux-mêmes choisis principalement parmi l'acide méthanesulfonique, l'acide trifuorométhanesulfonique, l'acide benzènesulfonique, l'acide benzylsulfonique, l'acide p-toluènesulfonique et l'acide camphresulfonique; HX fournit les conditions acides permettant d'obtenir un sel correspondant à l'imidate de formule (lc) Image ; b) hydrolyser le composé de formule (lc) pour obtenir ledit composé de formule (1).

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