Hydrochloric Acid → 6-Azaindole

Participants

Reaction Conditions

Reaction Steps

The azaindoline (step b, 1.1 g, 5.0 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 5.5M hydrochloric acid (5 ml). The mixture was heated at 50° C. for 4.5 hours cooled to 0° C. and basified with 5M sodium hydroxide (7.0 ml). The mixture was extracted with ethyl acetate (2×20 ml) and the combined ethyl acetate fractions were washed with saturated brine (20 ml), dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound as a pale yellow crystalline solid; yield: 0.57 g (97%). mp. 132°-134° C.[Lit. mp 131°-132° C.].

Provenance & Evidence