Process for the preparation of n-(4-hydroxyphenyl)- retinamide

Details Process for the preparation of n-(4-hydroxyphenyl)- retinamide Process for the preparation of n-(4-hydroxyphenyl)- retinamide

C - Chemistry, Metallurgy

07

C

C07C 403/18 (2006.01) C07C 231/02 (2006.01) C07C 403/20 (2006.01)

Patent

CA 2167582

This invention is directed to an efficient, mild, high yield process for the large scale synthesis of N-(4-hydroxyphenyl)-retinamide comprising the preferred steps of reacting retinoic acid with dimethylchloroformamidinium chloride to form retinoyl chloride which in turn is reacted with bis-(N, O)- trimethylsilyl-p-aminophenol to eventually form N-(4-hydroxyphenyl)-retinamide and to the novel use of bis-(N, O)-trimethylsilyl-p-aminophenol to eventually form a hydroxyphenylamide, particularly N-(4-hydroxyphenyl)-retinamide and methods of recrystallizing N-(4-hydroxyphenyl)-retinamide to obtain the stable "A" polymorph thereof.

Cette invention concerne un procédé efficace, doux et à haut rendement permettant la synthèse à grande échelle du N-(4-hydroxyphényl)-rétinamide. De préférence, on fait réagir de l'acide rétinoïque avec du chlorure de diméthylchloroformamidinium pour former le chlorure de rétinoyle que l'on fait réagir à son tour avec du bis-(N,O)-triméthylsilyl-p-aminophénol pour former finalement le N-(4-hydroxyphényl)-rétinamide. L'invention concerne aussi la nouvelle utilisation du bis-(N,O)-triméthylsilyl-p-aminophénol pour former un hydroxyphénylamide, en particulier le N-(4-hydroxyphényl)-rétinamide et des procédés de recristallisation du N-(4-hydroxyphényl)-rétinamide permettant d'obtenir le polymorphe stable "A" de celui-ci.

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