4,5-Dichloro-3,6-dihydroxybenzene-1,2-dicarbonitrile → HCID 66915158, compound

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Reaction Steps

2,3-Dichloro-5,6-dicyanohydroquinone (1.02 g, 4.50 mmol) was added to the solution of 4-fluoro-5-nitro-2,3-dihydro-indole (0.47 g, 2.25 mmol) in benzene (30 mL) and the mixture was refluxed for 7 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was washed with water (3×10 mL), brine (3×10 mL), dried over anhydrous sodium sulphate and concentration in vacuo afforded the crude product. Purification by column chromatography over neutral alumina using 5% ethyl acetate in hexane as eluent afforded 1-ethyl-4-fluoro-5-nitro-indole (0.33 g, 72%) as yellow solid.

Provenance & Evidence