Nitrogen → methyl 2-[3-(1-pyridin-3-ylethenyl)-1H-indol-2-yl]acetate

Participants

Reaction Steps

A solution of 6.13 g (0.032 m) of methyl indole-2 acetate, 7.16 g (7.0 mL, 0.059 m) of 3-acetylpyridine, and 10 mL of concentrated H2SO4 in 200 mL of dry MeOH was refluxed for 2 hours in an atmosphere of N2. The clear red solution was poured onto 600 g of ice. It was made alkaline with NH4OH and extracted with 2×500 mL portions of ether. The ether solution was washed with H2O, dried, and concentrated to dryness. The residue was triturated with hexane-ether (1:1), and the crystals that formed were collected and dried; wt 8.0 g; mp 154°-157° C. (lit. mp 160°-161° C.). The material was suitable for the next step. An additional 110 mg separated from the ether-hexane filtrate. Total yield 8.17 g.

Provenance & Evidence