Hydrochloric Acid → HCID 135773202, compound

Participants

Reaction Steps

Methyl 6-acetyl-4-chloro-7-hydroxy-8-propyl-quinoline-2-carboxylate (1.5 g) was treated with aniline (20 ml) at 175° C. in an autoclave in the presence of p-toluene sulphonic acid (0.1 g) for 72 hours. On cooling the aniline was removed and the residue was heated on a steambath for 12 hours with 70% sulphuric acid. The reaction mixture was poured onto crushed ice and neutralised with ammonia solution to pH 7. Extraction with ethyl acetate followed by drying and evaporation afforded a gum which was taken up in dry ethanol and saturated with hydrogen chloride gas while refluxing for 1 hour. Evaporation of the solvent and trituration with ether afforded the sub-title compound (0.37 g) identified by NMR and mass spectroscopy.

Provenance & Evidence