Benzocycloalkenecarboxylic acid and process for its preparation
AssigneeCiba-Geigy Corporation
InventorsAndreas von Sprecher, Hansjurg Wetter
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AssigneeCiba-Geigy Corporation
InventorsAndreas von Sprecher, Hansjurg Wetter
Estimating the term…
The novel (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic i.e. the compound of the formula ##STR1## in free form or in salt form, can be used as active ingredient in pharmaceutical preparations and can be prepared by a novel process, which is characterized in that racemic 4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid is reacted at elevated temperature with at least the equimolar amount of quinine in an alcoholic solvent for from approximately 6 to approximately 48 hours, the quinine salt of the (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid, precipitated in crystalline form as the direct reaction product, is separated from the reaction mixture, and the (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid is set free from this salt by acid treatment in a customary manner, and, if desired, this free acid is converted into a salt.
A process for the preparation of (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid, i.e. the compound of the formula ##STR3## in free form or in salt form, characterised in that racemic-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid is reacted at elevated temperature with at least the equimolar amount of quinine in an alcoholic solvent for from approximately 6 to approximately 48 hours, the quinine salt of the (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid, precipitated in crystalline form as the direct reaction product, is separated from the reaction mixture, and the (S)-4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid is set free from this salt by acid treatment in a customary manner, and, if desired, this free acid is converted into a salt.
A process according to characterised in that approximately 8 to approximately 50 ml of the alcoholic solvent are used per g of racemic 4-(2-bromobenzoyl)-5-hydroxy-benzocyclobutene-1-carboxylic acid.
Dependencies are inferred from the claim text.