Patent GB-351605-A (GB)
Title: Manufacture of amino-alkoxy-compounds useful as antiseptics
IPC: C07D215/18
Filed: 1930-04-07
Abstract: Aminoalkoxy aromatic and quinoline compounds containing nuclear halogen are prepared by (1) treating an aromatic or quinoline compound containing nuclear halogen and a nuclear hydroxyl group with an aminoalkylating agent; (2) interaction of an aminoalcohol with a polyhalogen aromatic or quinoline compound in such a manner that at least one nuclear halogen remains in the product; (3) introducing halogen into the nucleus of an aminoalkoxy compound of the aromatic or quinoline series, e.g. by direct halogenation, or by replacing a nuclear amino group by halogen via the diazo group; (4) converting an aromatic aminoalkoxy compound containing nuclear halogen into the corresponding quinoline compound, e.g. by treatment of an amino derivative of the said aromatic compound with glycerine and a condensing agent.  The products, which form water-soluble salts, are useful therapeutically.  Examples are given of the preparation of (1) 1-diethylaminoethoxy-2-isopropyl-4-chloro-5-methylbenzene from chlorothymol and chlorethyldiethylamine; (2) 2 : 4 : 6-tribromo - 1 - diethylaminoethoxybenzene from tribromophenol and chlorethyldiethylamine; (3) a 1-diethylaminoethoxy-bromonaphthalene by the bromination of 1-diethylaminoethoxy-naphthalene, obtained from a -naphthol and chlorethyldiethylamine; (4) 1-diethylaminoethoxy-2-amino-4-chlorobenzene from 2-amino - 4 - chlorophenol and chlorethyldiethylamine; (5) 5-chloro-7-iodo-8-diethylaminoethoxy-quinoline from 5-chloro - 7 - iodo - 8 - oxyquinoline and chlorethyldiethylamine; (6) 5 : 6 : 7 - trichloro - 8 - diethylaminoethoxy-quinoline from 5 : 6 : 7-trichloro-8-oxyquinoline and chlorethyldiethylamine; (7) 2-diethylaminoethoxy - 4 - methyl - 7 - chloroquinoline from 2 : 7-dichloro-4-methylquinoline and diethylaminoethanol; (8) 5-chloro-8-diethylaminoethoxy-quinoline from 1-diethylaminoethoxy-2-amino-4-chlorobenzene by condensation with glycerine in presence of arsenic acid and sulphuric acid.  In a similar manner the following compounds are prepared:-1-dicyclohexylaminoethoxy - 4 - chlorobenzene, 5-bromo-8-diethylaminoethoxy-quinoline, 5-chloro-8-dicyclohexylaminoethoxy-quinoline, 5-chloro - 7 - bromo - 8 - diethylaminoethoxy-quinoline, 5 : 7-dibromo - 8 - diethylaminoethoxy-quinoline, 5-bromo-7-iodo-8-diethylaminoethoxy-quinoline and 5 : 7-diiodo-8-diethylaminoethoxy-quinoline.  Quinoline derivatives.  2 : 7-Dichloro-4-methyl-quinoline is prepared by condensing m-chloraniline with acetoacetic ester, effecting ring closure by heating with sulphuric acid, and heating the resulting 2-oxy-4-methyl-7-chloroquinoline with phosphorus oxychloride.  5 - Chloro-7 - bromo - 8-oxyquinoline results from the bromination of 5-chloro-8-oxyquinoline.  5 - Bromo - 7 - iodo - 8 - oxyquinoline is obtained by treating sodium 5-bromo-8-oxyquinoline with a solution of iodine in aqueous sodium iodide; similar treatment of 8-oxyquinoline yields 5 : 7-diiodo-8-oxyquinoline.  Chlorethyldicyclohexylamine is prepared by heating dicyclohexylaminoethanol, obtained by interaction of dicyclohexylamine and glycol chlorhydrin, with thionyl chloride.