Process for preparing 2-oxindoles and n-hydroxy-2-oxindoles

Details Process for preparing 2-oxindoles and n-hydroxy-2-oxindoles Process for preparing 2-oxindoles and n-hydroxy-2-oxindoles

C - Chemistry, Metallurgy

07

D

C07D 209/34 (2006.01) C07C 201/12 (2006.01) C07C 205/56 (2006.01) C07D 209/60 (2006.01) C07D 209/70 (2006.01) C07D 491/04 (2006.01) C07D 495/04 (2006.01)

Patent

CA 2210695

The present invention provides processes having practical utility for preparing 2-oxindoles, N-hydroxy-2-oxindoles, or mixtures thereof comprising: catalytically hydrogenating a 2-nitroarylmalonate diester to produce a 2-(N-hydroxyamino)arylmalonate diester, a 2-aminoarylmalonate diester, or mixtures thereof as a first reaction intermediate: cyclizing, by intramolecular aminolysis of one ester group, the first reaction intermediate to produce a N-hydroxy-2-oxindole-3-carboxylate ester, 2-oxindole-3-carboxylate ester, or mixtures thereof as a second reaction intermediate; and hydrolyzing and decarboxylating the remaining ester group of the second reaction intermediate to produce the N-hydroxy-2-oxindole, the 2-oxindole, or mixtures thereof, wherein the cyclization reaction and the hydrolysis and decarboxylation reaction are conducted in situ with the catalytic hydrogenation reaction without isolation of said reaction intermediates.

La présente invention concerne des procédés particulièrement utiles, permettant de préparer des 2-oxindoles, des N-hydroxy-2-oxindoles ou leurs mélanges, consistant à hydrogéner, en présence d'un catalyseur, un diester 2-nitroarylmalonique pour produire dans un premier temps un diester 2-(N-hydroxyamino)arylmalonique, un diester 2-aminoarylmalonique et leurs mélanges, à procéder à une cyclisation par aminolyse intramoléculaire d'un groupe ester du produit obtenu dans la première étape, pour obtenir dans cette seconde étape un ester N-hydroxy-2-oxindole-3-carboxylique, un ester 2-oxindole-3-carboxylique ou un mélange de ceux-ci, et à hydrolyser et décarboxyler le groupe ester restant du second intermédiaire de réaction pour produire la N-hydroxy-2-oxindole, la 2-oxindole ou leurs mélanges. Dans ce procédé, la réaction de cyclisation, l'hydrolyse et la décarboxylation se font dans le réacteur d'hydrogénation sans séparation des produits des réactions intermédiaires.

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