2,4-Dimethylaniline → Aniline

Participants

Reaction Conditions

Reaction Steps

To a solution containing 0.60 g (2.57 mmol) of 3-bromo-1-methyl-5-nitropyridin-2(1H)-one in 120 ml of toluene under a nitrogen atmosphere was added 0.64 ml (5.15 mmol) of 2,4-dimethylaniline, 1.61 g (2.57 mmol) of rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (racemic BINAP), 0.37 g (3.85 mmol) of sodium t-butoxide and 1.20 g (1.31 mmol) of tris(dibenzylideneacetone)dipalladium (0). The reaction was heated to 95° C. overnight. The reaction was cooled to room temperature, diluted with ethyl acetate and washed with saturated sodium bicarbonate. The organic phase was dried over magnesium sulfate. Filtration, removal of solvent and purification of the residue via biotage eluting with 60% ethyl acetate/hexanes gave the desired product with some starting aniline. The material was triturated with hexanes and the solids filtered and dried to afford 0.154 g (21.9%) of product.

Provenance & Evidence