Hydrochloric Acid → 4-(7-Chloro-4-aminoquinolyl)-2-diethylaminomethyl-5,6,7,8-tetrahydro-1-naphthol

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Reaction Steps

A solution of 2 g of 2-diethylaminomethyl-4-acetamino-5,6,7,8-tetrahydro-I-naphthol, and 50 ml of concentrated hydrochloric acid in 200 ml of absolute ethanol was refluxed for 12 hours. Thereafter the solvent was distilled and the residue treated with ammonium hydroxide then extracted with ether. The etherial extract was washed with water and dried over magnesium sulphate. Then the ether was distilled to reside the amine. From this residual amine 6 g was mixed with 4 g of 4,7-dihchloroquinoline and few drops of conc. HCl in 50 ml of absolute ethanol and refluxed for 12 hours. Thereafter, the reaction mixture was cooled and diluted with water to double its volume then poured over a cold solution of ammonia. The formed precipitate was collected and washed with water. After drying, it weighed 9.2 g (90 % yield) of 4-(7-chloro-4-quinolylamino)-2-diethylaminomethyl-5,6,7,8-tetrahydro-I-naphthol (III). After recrystallization, it melted at 215°-217°C.

Provenance & Evidence