Tetrahydrofuran → 4'-bromo-N-methyl-2'-aminobenzanilide

Participants

Reaction Steps

9.5 g (28 mmol) of 4′-bromo-N-methyl-2′-nitro-benzanilide were dissolved into 100 mL of tetrahydrofuran. While the solution was stirred at room temperature in an argon atmosphere, a solution of 25 g (142 mmol) of sodium hydrosulfite in 90 mL of water was added. Furthermore, 10 mL of methanol were added, and the whole was stirred for 3 hours. Next, 100 mL of ethyl acetate were added, and then a solution of 12 g (142 mmol) of sodium hydrogen carbonate in 125 mL of water was added. After having been stirred for 1 hour, the resultant was extracted with ethyl acetate. An aqueous layer was removed, and an organic layer was washed with a 10-mass % aqueous solution of K2CO3 and a saturated sodium chloride solution, and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, with the result that 7.8 g of 4′-bromo-N-methyl-2′-amino-benzanilide were obtained as a white solid (90% yield). The coarse product was directly used for the next reaction.

Provenance & Evidence