Ethanol → 1-amino-8-fluoro-5H-pyrido[4,3-b]indole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-chloro-8-fluoro-5H-pyrido[4,3-b]indole-4-carbonitrile in a 1:1 (v/v) mixture of EtOH and conc. NH4OH (0.13 M) was heated in a microwave reactor at 150° C. for 1 h in a sealed tube. After cooling to room temperature, the suspension was diluted with H2O and filtered. The crude material was placed in a flask cooled to 0° C. before conc. H2SO4 (excess) was added dropwise under vigorous stirring. The final mixture was warmed to room temperature and, after 4 h, poured carefully into a diluted aqueous solution of NH4OH cooled to 0° C. The precipitate was collected by filtration and was purified by flash chromatography (20-50% ethanol in CH2Cl2) to provide the title compound as an off-white solid.

Provenance & Evidence