5-(Tert-butyl-dimethyl-silanyloxy)-2-nitro-aniline → 4-((tert-Butyldimethylsilyl)oxy)benzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

A solution of 5-(tert-butyl-dimethyl-silanyloxy)-2-nitro-aniline (1.9 g, 7.08 mmol) in methanol (40 ml) is introduced in a hydrogenation vessel with 10% palladium on carbon catalyst (0.226 g). The reaction mixture is heated at 80° C. for 3 hours under an hydrogen atmosphere (P=1 bar). The reaction mixture is then filtered on Celite® and concentrated under reduced pressure. The residue is dissolved in 10 ml of ethyl acetate and filtered through a silica gel plug (40 ml) that is washed with 600 ml of ethyl acetate. The organic filtrates are concentrated under vacuum to yield 2.55 g of 4-(tert-butyl-dimethyl-silanyloxy)-ortho-phenylenediamine used without further purification in the following step. Analytical LC/MS (method B): retention time=3.12 min., m/z=239.15 (positive ion mode).

Provenance & Evidence