Sodium Dithionite → N-(3-amino-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

To a solution of the above-mentioned crude product of 3-(1-cyano-1-methylethyl)-N-(4-methyl-3-nitrophenyl)benzamide in tetrahydrofuran (300 mL) was added an aqueous solution (500 mL) of sodium dithionite (78.1 g, 629 mmol), and the mixture was stirred at 100° C. for 2 hr. The organic layer of the reaction mixture was separated, and the aqueous layer was extracted with ethyl acetate (2×150 mL). The combined organic layer was washed with saturated brine (150 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→0/100), and the fractions containing the object product were concentrated under reduced pressure to give the title compound (5.60 g, 38%) as a yellow solid.

Provenance & Evidence