Preparation of aromatic ketones having cardiovascular activity

Details Preparation of aromatic ketones having cardiovascular activity Preparation of aromatic ketones having cardiovascular activity

C - Chemistry, Metallurgy

07

C

260/579.2

C07C 97/10 (1980.01)

Patent

CA 1061801

PREPARATION OF AROMATIC KETONES HAVING CARDIOVASCULAR ACTIVITY ABSTRACT OF THE DISCLOSURE Compounds of the formula: Image in which R1 and R2 each is an alkyl group having 1 to 4 carbon atoms and R4 is a halogen atom having therapeutic value in the treatment of cardiovascular conditions are formed by reacting a substituted salicylic aldehyde of the formula: Image with a 1-alkylamino-2-hydroxy-3-chloropropane of the formula: C1CH2.CHOH.CH2NHR in an anhydrous solvent in the presence of a dehydrating agent, treating the resulting 3-alkyl-5-chloromethyl-2- (orthohydroxyphenyl)oxazolidine in a dipolar aprotic solvent with a basic agent to produce an 8-aza-4,9- dioxa-2,3-benzo-[4,2,1]-bicyclooctane, subjecting the latter material to acid hydrolysis to produce a 2-(3-alkyl- amino-2-hydroxypropoxy) benzaldehyde, reducing the benzaldehyde to the corresponding benzyl alcohol and oxidizing the benzyl alcohol with chromic acid in the presence of sulphuric acid.

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