Hydrochloric Acid → 4-[(6a-Methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoic acid

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Reaction Steps

A suspension of ethyl 4-[(6a-methyl-5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)amino]benzoate (0.250 g) in ethanol (15 ml) was added with 20% aqueous sodium hydroxide (5 ml), and the mixture was stirred overnight at room temperature. The reaction mixture was made acidic with 2 N aqueous hydrochloric acid, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure, and the resulting residue was recrystallized from ethyl acetate-n-hexane to obtain the title compound (0.185 g, yield: 80%) as pale brown needles (melting point: 232-234° C.).

Provenance & Evidence