Isobutyl chloroformate → HCID 131715971, compound

Participants

Reaction Steps

Isobutyl chloroformate (1.5 ml) was added dropwise to a stirred solution of 5-amino-1H-indole-3-acetonitrile (1.7 g) in dry DMF (20 ml). After 10 min the solution was diluted with water (150 ml) and stirring continued for 30 min. The resulting solution was extracted with ethyl acetate (2×100 ml) and the combined extracts washed with brine (10%, 100 ml), water (100 ml), dried (Na2SO4) and evaporated in vacuo to yield the crude product as a brown oil. This was purified by column chromatography (Kieselgel 60, 100 g) using ether as the eluent, to give the title compound as a colourless gum (1.08 g) which darkened to a brown gum on storage. This material failed to crystallise from common organic solvents.

Provenance & Evidence