Formamide → N-(1,3,4,9-tetrahydro-2H-carbazol-2-yl)formamide

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Reaction Steps

A mixture of 8.90 g (0.048 mol) of 2,3,4,9-tetrahydro-1H-carbazol-2-amine and 65 ml of dry formamide was stirred and heated under N2 for 5 hr at 95°-100° C. The cooled reaction mixture was poured into H2O, and the precipitated gum extracted with CHCl3. The combined extracts were washed with 0.1 N HCl, 5% aqueous NaHCO3, and H2O, and dried. Et2O-trituration of the residue remaining after evaporation of the CHCl3 gave a tan solid, 8.58 g, mp 123°-126°. For analysis, it was necessary to dry the recrystallized (EtOH) sample at 120° (P2O5, 0.02 mm, 20 hr), mp 169°-171°.

Provenance & Evidence