Hydrochloric Acid → HCID 13362120, compound

Participants

Reaction Steps

To a suspension of p-hydrazinohydrocinnamic acid (Manske and Kulka, J. Can. Res., 25B: 376 (1947), 4.50 g) in 50 ml of absolute ethanol under nitrogen at room temperature was added while stirring 10 ml of a saturated ethanolic hydrogen chloride solution. A solution resulted in approximately 5 minutes. To the red-orange solution was added 3-propionylpyridine (3.37 g, 0.025 mole), the reaction mixture was heated to reflux and maintained at reflux for 18 hours. The resulting solution was cooled in an ice-water bath and the resulting yellow crystals of ethyl 3-methyl-2-(3-pyridyl)indole-5-propionate hydrochloride were collected, m.p. 249°-51°. The free base, ethyl 3-methyl-2-(3-pyridyl)indole-5-propionate was prepared by suspending the hydrochloride salt in water, basifying with 3N sodium hydroxide and extracting with ether.

Provenance & Evidence