Hydrochloric Acid → 2-Methoxybenzoic acid

Participants

Reaction Steps

6 g of triethylamine and 1.9 g of chloroformic acid methyl ester are added, while stirring and cooling with ice, to 5 g of 5-chloro-2-cyclohexyloxy-nicotinic acid in 150 ml of tetrahydrofuran. Stirring is continued for 30 minutes at 0° C. and, while stirring, 4.6 g of 4-(2-aminoethyl)-2-methoxybenzoic acid are added in the form of its hydrochloride. The mixture is further stirred for 4 hours at room temperature, the solvent removed under reduced pressure, the residue reprecipitated from ammonia and recrystallized from ethanol or ethyl acetate. The 4-(2-<5-chloro-2-cyclohexyloxy-nicotinamido>-ethyl)-2-methoxy-benzoic acid obtained melts at 170°-172° C.

Provenance & Evidence