Patent GB-270339-A (GB)
Title: Manufacture of derivatives of substituted quinoline carboxylic acids
IPC: C07D215/50
Filed: 1927-04-30
Abstract: 270,339. Soc. of Chemical Industry in Basle. April 30, 1926, [Convention date]. Halogen, oxy and amino derivatives of quinoline carboxylic acid amides.-alpha-Halogenquinolinecarboxylic acid amides are prepared by reacting upon an a-halogenquinolinecarboxylic acid halide with ammonia, a primary or secondary amine, or a derivative thereof. The halogen group of the product is then replaced either by all:oxy or phenoxy groups by treatment with an alcoholate (or alcoholic alkali), phenolate or derivative, or by amino or substituted amino groups by treatment with ammonia or primary or secondary base, or a derivative thereof. The amino derivatives of the acid amides mav also be obtained directly by interaction of the alpha-halogenquinoline-gamma-carboxylic acid halides with the requisite amount of ammonia, or primary or secondary amine at temperatures above about 100‹ C. The compounds possess therapeutic properties. The preparation of the following alphachloroquinoline-gamma-carboxylic acid amides is described, viz. the dimethylamide, the diethylamide and the diethylethylenediamide by reacting on a - chloroquinoline-y-carboxylic acid chloride with dimethylamine, diethylamine and asymmetrical diethylethylenediamine respectively; the dipropylamide, diallyamide. diisoamylamide, piperidide, N-ethylanilide, monoethylamide and benzylamide are obtained in an analogous manner. Examples are also given of the preparation of the following alpha-alkoxy and alpha-phenoxy derivatives of quinoline-gamma-carboxylic acid amides, viz. a-ethoxyquinoline-y-carboxylic acid dimethylamide, alpha-cyclohexyloxyquinoline - y - carboxylic acid diethylamide alpha-phenoxyquinoline-gammacarboxylic acid diethylamide, alpha-diethylaminoethoxyquinoline-gamma-carboxylic acid diethylamide, alpha-ethoxyquinoline-gamma-carboxylic acid diethylethylenediamide and alphaethoxyquinoline-gamma-carboxylic acid amide by treatment of the corresponding alpha-chloro body with sodium alcoholate or a solution of alkali hydroxide in aqueous alcohol, sodium cyclohexanolate, sodium phenolate, sodium diethylaminoethanolate., sodium alcoholate, and sodium alcoholate respectively. From the corresponding a-chloroquinoline-y-carboxylic acid amides the following may be similarly prepared :-the alpha-methoxy, ethoxy, propyloxy, isopropyloxy, allyloxy and phenethoxy derivatives of quinoline-gamma-carboxylic acid diethylamide, and the alpha-ethoxy derivatives of quinoline-gamma-carboxylic acid dipropylamide, diallylamide, diisoamylamide, piperidide, N-ethylanilide, monoethylamide and benzylamide. The preparation of alphadiethylaminoquinoline-gamma-carboxylic acid diethylamide by treating the alpha-chloro body with diethylamine is also described; the base may be made directly from alpha-chloroquinoline-gamma-carboxylic acid chloride by treatment with the requisite proportions of diethylamine. The Specification as open to inspection under Sect.. 91 (3) (a) includes the treatment of gamma-halogenquinotinecarboxylic acid halides or their substitution products with ammonia, a primary or secondary base or a derivative thereof; the said products, or those prepared in any other way, are then optionally treated with an alcoholate, a phenolate, ammonia, a primary or secondary base, or a derivative thereof. This subject-matter does not appear in the Specification as accepted.