Quinoline → 4-Methyl-1h-indole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

4.71 g (18.5 mmol) of 5-bromo-4-methyl-1H-indole-2-carboxylic acid and 5.03 g (56.2 mmol) of cuprous cyanide were dissolved in 35 ml of quinoline and the solution heated at 230° C. for 90 minutes. The reaction mixture was then cooled down to ambient temperature and poured onto crashed ice. The pH was adjusted to pH 2-3 and the mixture subsequently extracted 3 times with ether. The combined organic phases were washed with water, dried over magnesium sulfate and evaporated to give a crude product which was purified by chromatography (silicagel, eluent: gradient of n-heptane/ethyl acetate) to yield 2.36 g of 4-methyl-1H-indole-5-carbonitrile as light brown solid.

Provenance & Evidence