2-{[Tert-butyl(dimethyl)silyl]oxy}-6-nitroaniline → 3-[(Tert-butyldimethylsilyl)oxy]benzene-1,2-diamine

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Reaction Steps

To a solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-6-nitroaniline (8.5 g, 31.7 mmol) in tetrahydrofuran (100 mL) is added a 10% palladium on carbon (50% wet, 8.2 g), and the mixture is vigorously stirred under hydrogen atmosphere at room temperature for one hour. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (ethyl acetate/n-hexane=1/5, 1/3 and 1/1) to give the title compound as brown oil (6.95 g, yield: 92%).

Provenance & Evidence