7-methyl-6-nitro-1H-indole → 7-methyl-1H-indol-6-amine

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Reaction Steps

A degassed suspension of 7-methyl-6-nitroindole (1.5 g, 8.5 mmol) and catalytic 10% palladium on carbon in ethanol (75 mL) is placed under an atmosphere of hydrogen at 50 p.s.i. for 7 hours. The reaction mixture is filtered through Celite and the mixture concentrated by rotary evaporation. The crude residue is purified via silica gel column chromatography using 20% isopropanol/hexanes as the eluting solvent. The product containing fractions are combined and the solvents removed by rotary evaporation to yield 0.95 g of 6-amino-7-methylindole as a light brown solid (76% yield).

Provenance & Evidence