Patent GB-355017-A (GB)
Title: Manufacture of n-substituted derivatives of the pyridone series
IPC: C07D213/64
Filed: 1930-08-11
Abstract: N-Aminoalkyl-pyridones, -quinolones, and -isoquinolones are prepared by (1) converting pyridones, quinolones, or isoquinolones whose nuclear nitrogen is linked with hydrogen, or compounds containing the 2- or 4-oxypyridine nucleus, into said products by treatment with a reactive ester of an aminoalcohol, or by first converting into the N-alkylhalogen derivative and treating this with ammonia or an amine; (2) converting compounds containing the 2- or 4-oxypyridine nucleus into their aminoalkoxy derivatives and then isomerizing by heat treatment; (3) interaction of compounds containing a pyridine nucleus having a free 2- or 4- position with an aminoalcohol ester and oxidizing the product, chemically or electrolytically; (4) interaction of a pyrone with an alkylene polyamine having at least one primary amino group.  The products are useful as, or in the manufacture of, therapeutic compounds. According to the examples (1) N-diethylaminoethyl-2-pyridone is prepared by treating sodium 2-pyridone with chlorethyldiethylamine, or by heating 2-diethylaminoethoxypyridine to 220-270 DEG  C.; the same product results when the reaction product of pyridine with chlorethyldiethylamine is oxidized with potassium ferricyanide; (2) N-diethylaminoethyl-2-pyridone-3-carboxylic acid-anilide is obtained by heating 2-diethylaminoethoxy-3-pyridone-carboxylic acidanilide; similar treatment of 2-diethylaminoethoxylepidine, obtained from 2-chlorolepidine and sodium diethylaminoethylate, yields N-diethylaminoethyllepidone; (3) N-diethylaminoethyl-2-quinolone-4-carboxylic acid-anilide is formed when 2-oxy-4-quinoline-carboxylic acid-anilide, obtained by partial saponification of 2-chloro-4-quinoline-carboxylic acid-anilide, is treated with chlorethyldiethylamine; (4) 2-chloro-3-phenyl-4-quinoline-carboxylic aciddiethylamide, obtained by treating the corresponding acid chloride with diethylamine, is reacted with sodium diethylaminoethylate and the resulting 2-diethylaminoethoxy - 3 - phenyl - 4 - quinoline-carboxylic acid-diethylamide then isomerized by heat treatment to N-diethylaminoethyl-2-quinolone-3-phenyl-4-carboxylic acid-diethylamide; (5) N-diethylaminoethyl-4-pyridone is obtained by heating 4-pyrone with diethylethylenediamine.  By isomerization treatment, 2-dimethylaminoethoxy-3-pyridine-carboxylic acid-anilide may be converted into N-dimethylaminoethyl-2-pyridone-3-carboxylic acid-anilide, 2-n-dibutylaminoethoxy-3-pyridinecarboxylic acid-anilide into N-dibutylaminoethyl-2-pyridone-3-carboxylic acid-anilide, 2-piperidinoethoxy-3-pyridine-carboxylic acid-anilide into N-piperidinoethyl-2-pyridone-3-carboxylic acid-anilide, 2-diethylaminoethoxy-3-pyridine-carboxylic acidphenetidide into N-diethylaminoethyl-2-pyridone-3-carboxylic acid-phenetidide, 2-diethylaminoethoxy-3-pyridine-carboxylic acid-N-ethylanilide into N-diethylaminoethyl-2-pyridone-3-carboxylic acid-N-ethylanilide, and 2-diethylaminoethoxy-3-pyridine-carboxylic acid-diethylethylenediamide into N-diethylaminoethyl - 2 - pyridone-3-carboxylic acid-diethylethylenediamide. N-Aminoalkyl-acridones.-The Specification as open to inspection under Sect. 91 (3) (a) states that the above processes are applicable to the preparation of N-aminoalkyl-acridones.  This subject-matter does not appear in the Specification as accepted. 2-Diethylaminoethoxy-3-pyridine-carboxylic acid-anilide is prepared from 2-hydroxy-3-pyridine-carboxylic acid by treatment with phosphorus pentachloride, interaction of the resulting 2-chloro-3-pyridine-carboxylic acid chloride with aniline and conversion of the anilide with sodium diethylaminoethylate.