Hydrochloric Acid → 5-Cyanotryptamine

Participants

Reaction Steps

Add zinc powder (16.22 g, 248.1 mmol) in four portions to 2N HCl (300.0 ml). Add dropwise 3-(2-nitroethyl)-5-cyano-1H-indole (2.25 g, 10.5 mmol) as a solution in methanol (300.0 ml). Heat to reflux. After 2.5 hours, cool to ambient temperature and adjust the pH to 11 using 5N NaOH, filter through Celite, wash with water, then extract the filtrate with dichloromethane. Combine the organic extracts, wash with brine, dry (Na2SO4), then evaporated to give the title compound: mp 102–105° C., MS (ACPI): m/e 186.1 (M+1). Analysis for C11H11N3: Calcd: C, 71.33; H, 5.99; N, 22.69; found: C, 71.03; H, 5.91; N, 22.64.

Provenance & Evidence