Method for the preparation of 5-cyanophthalide

C - Chemistry – Metallurgy – 07 – D

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C07D 307/87 (2006.01) C07D 307/88 (2006.01)

Patent

CA 2356188

A method for the preparation of 5-cyanophthalide in which 5-carboxyphthalide is converted to the corresponding amide of Formula (IV) in which R is hydrogen or C1-6 alkyl, which is then reacted with a dehydrating agent thereby obtaining 5-cyanophthalide. The conversion of 5-carboxyphthalide to the corresponding amide of Formula (IV) may be carried out via the corresponding C1-6alkyl or phenyl ester or the acid chloride, which is converted to the amide of Formula (IV) by amidation with ammonia or a C1-6 alkylamine. By the process 5-Cyanophtalide, an important intermediate used in the preparation of the antidepressant drug citalopram, is prepared in high yields by a convenient, cost effective procedure.

L'invention concerne une technique permettant de préparer un 5-cyanophtalide qui est converti en amide correspondant représenté par la formule (IV). Dans cette formule, R représente hydrogène ou alkyle C1-6, qui est ensuite mis à réagir avec un agent déshydrateur, ce qui permet d'obtenir le 5-cyanophtalide. La conversion du 5-carboxyphtalide en amide correspondant représenté par la formule (IV) peut être réalisée via les alkyle C1-6, éther de phényle ou chlorure d'acide correspondants convertis en amide représentés par formule (IV), par amidation avec de l'ammoniac ou un alkylamine C1-6. Lors du traitement de 5-Cyanophtalide, un intermédiaire important utilisé pour préparer le citaloprame, médicament antidépressif, est préparé selon des rendements élevés, et une procédure appropriée et bon marché.

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