A process for the preparation of...

Details A process for the preparation of... A process for the preparation of...

C - Chemistry, Metallurgy

07

D

C07D 215/26 (2006.01)

Patent

CA 2520990

The invention relates to a process for preparing 5-(.alpha.-haloacetyl)-8- substituted oxy-(1H)-quinolin-2-ones. The process involves (i) reacting (a) 8- hydroxy-(1H)-quinolin-2-one with an acylating agent and a Lewis acid to form 5- acetyl-8-hydroxy-(1H)-quinolin-2-one; or (b) 8-hydroxy-(lH)-quinolin-2-one with an acylating agent to form 8-acetoxy-(lH)-quinolin-2-one, and treating, in-situ, the 8-acetoxy-(1H)-quinolin-2-one with a Lewis acid to form 5-acetyl- 8-hydroxy-(1H)-quinolin-2-one; or (c) 8-acetoxy-(1H)-quinolin-2-one with a Lewis acid to form 5-acetyl-8-hydroxy-(lH)-quinolin-2-one; (ii) reacting the 5- acetyl-8-hydroxy-(1H)-quinolin-2-one prepared in Step (i) with a compound having the Formula RL in the presence of a base and a solvent to form 5-acetyl- 8-substituted oxy-(1H)-quinolin-2-one, wherein R is a protecting group and L is a leaving group; and (iii) reacting the 5-acetyl-8-substituted oxy-(1H)- quinolin-2-one with a halogenating agent in the presence of a solvent to form a 5-(.alpha.-haloacetyl)-8-substituted oxy-(1H)-quinolin-2-one.

La présente invention a trait à un procédé de préparation de 5-(.alpha.-haloacétyl)-8-substitué oxy-(1<I>H</I>)-quinolin-2-ones. Le procédé comprend (i) la réaction de (a) 8-hydroxy-(1<I>H</I>)-quinolin-2-one avec un agent d'acylation et un acide de Lewis pour former du 5-acétyl-8-hydroxy-(1<I>H</I>)-quinolin-2-one; ou (b) 8-hydroxy-(1<I>H</I>)-quinolin-2-one avec un agent d'acylation pour former du 8-acétoxy-(1<I>H</I>)-quinolin-2-one, et le traitement, in situ, du 8-acétoxy-(1<I>H</I>)-quinolin-2-one avec un acide de Lewis pour former du 5-acétyl-8-hydroxy-(1<I>H</I>)-quinolin-2-one; ou (c) du 8-acétoxy-(1<I>H</I>)-quinolin-2-one avec un acide de Lewis pour former du 5-acétyl-8-hydroxy-(1<I>H</I>)-quinolin-2-one ; (ii) la réaction du 5-acétyl-8-hydroxy-(1<I>H</I>)-quinolin-2-one préparé à l'étape (i) avec un composé ayant la formule RL en présence d'une base et d'un solvant pour former du 5-acétyl-8-substitué oxy-(1<I>H</I>)-quinolin-2-one, dans laquelle R est un groupe protecteur et L est un groupe partant ; et (iii) la réaction du 5-acétyl-8-substitué oxy-(1<I>H</I>)-quinolin-2-one avec un agent d'halogénation en présence d'un solvant pour former un 5-(.alpha.-haloacétyl)-8-substitué oxy-(1<I>H</I>)-quinolin-2-one.

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