Hydrochloric Acid → N-ethyl-3-nitroaniline

Participants

Reaction Conditions

Reaction Steps

To a solution of 8 g (44 mmol) of 3-nitroacetanilide in 200 ml of dry THF, a solution of 5.5 ml (58 mmol) of borane dimethyl sulfide complex in 5 ml of THF was added, followed by stirring at 80° C. for 4 hours. To the reaction mixture, 3 ml (32 mmol) of borane dimethyl sulfide complex were further added, followed by stirring at 80° C. for 3 hours. After 1N hydrochloric acid was added to the reaction mixture until the solution became uniform, the solvent was concentrated under reduced pressure. To the residue, a 10N aqueous solution of sodium hydroxide was added, followed by extraction with chloroform. The extract was washed with saturated saline and then dried over magnesium sulfate. The solvent was distilled out under reduced pressure. The residue was purified by chromatography on a column (ethyl acetate/n-hexane=4/1), whereby 6.6 g of the title compound were obtained as brown powder (yield: 89%).

Provenance & Evidence