Patent GB-310074-A (GB)
Title: Manufacture of basic derivatives of substituted quinoline-carboxylic acids
IPC: C07D215/50
Filed: 1927-12-22
Abstract: 310,074. Soc. of Chemical Industry in Basle, and Miescher, K. Dec. 22, 1927. Addition to 270,339. Samples furnished. Halogen and oxy derivatives of quinolinecarboxylic acid amides. - Quinoline carboxylic acids containing (1) an unsymmetrical diethylethylenediamide group together with a substituted a-oxy group, the substituent containing more than two carbon atoms, or (2) a substituted a-oxy group together with an alkylenepolyamide residue containing at least one tertiary amino group, are prepared according to the process of the parent Specification. The products, which form neutral water-soluble salts, possess marked anaesthetic properties. According to the examples (1) a-chloro-y-quinolinecarboxylic aciddiethylethylenediamide is treated with the sodium compound of n-butyl alcohol, cyclohexanol or hydroquinone monomethylether to give a-n-butyloxy-a-cyclohexyloxy- or a-(p-methoxyphenoxy)-yquinolinecarboxylic acid - diethylethylenediamide respectively; (2) a-ethoxy- and a-isoamyloxy-yquinolinecarboxylic acid-triethylethylenediamide are obtained by interaction of a-chloro-y-quinolinecarboxylic acid-triethylethylenediamide (prepared by treating a-chloro-y-quinoline carboxylic acid chloride with triethylethylenediamine) with alcoholic sodium hydroxide and sodium amyl alcoholate respectively, (3) alpha-n-butyloxy-gamma-quinoline carboxylic acid-bis-(diethylaminoethyl)-imide is prepared by treating the corresponding a-chloro compound (obtained by reacting on a-chloro-y. quinolinecarboxylic acid chloride with bis-(diethylaminoethyl)-imine) with sodium n-butyl alcoholate; (4) alpha-ethoxy-gamma-quinolinecarboxylic acid N-methylpiperazide results from the interaction of the a-chloro compound (prepared by treating a-chloro-y-quinolinecarboxylic acid chloride with piperazine hydrate and dimethyl sulphate in presence of alkali hydroxide) with alcoholic potassium hydroxide. In an analogous manner, the following bases are obtained :-alpha-n-propyloxyaallyloxy-, a-n-amyloxy-, alpha-isoamyloxy-, a-n-heptyloxy-, a-benzyloxy, and a-phenethoxy-y-quinolinecarboxylic acid-diethylethylenediamide; a-ethoxygamma-quinolinecarboxylic acid-diethylpentamethylenediamide; a-n-butyloxy-y-quinolinecarboxylic acid-#-N-piperidylethylamide; a-methoxy-, a-npropyloxyalpha-n-butyloxy-, a-n-amyloxy-, a-cyclohexyloxy-, and a-benzyloxy-y-quinolinecarboxylic acid-triethylethylenediamide; a-butyloxy-y-quinolinecarboxylic acid-N-methylpiperazide; and aethoxy-y-quinolinecarboxylic acid-bis-(diethylaminoethyl)-imide. The alpha-chloro-gamma-quinolinecarboxylic acid-diethylpentamethylenediamide and - #-N-piperidylethylamide are obtained by causing alpha-chloro-gamma-quinolinecarboxylic acid chlordie to react with unsymmetrical diethylpentamethylenediamine or #-N piperidylethylamine respectively. Triethylethylenediamine is prepared by reducing ethylidene-diethylethylenediamine, a condensation product of unsymmetrical diethylethylenediamine and acetaldehyde. Bis-(diethylaminoethyl)-imine is obtained by interaction of #-chlorethyldiethylamine and ammonia.