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

Participants

Reaction Steps

Dissolving 9.5 g (28 mmol) of 4′-bromo-N-methyl-2′-nitro-benzanilide obtained in the above step (2) into 100 milliliter of tetrahydrofuran, and during agitation under the atmosphere of argon gas and at room temperature, a solution provided by mixing 25 g (0.14 mmol) of sodium hydrosulfite into 90 milliliter of water was added. Further, adding 10 milliliter of methanol, the resultant solution was stirred for 3 hours. Subsequently, adding 100 milliliter of ethyl acetate and then, a solution provided by mixing 12 g (0.14 mmol) of sodium hydrogen carbonate and 125 milliliter of water was further added. The resultant solution was stirred for 1 hour, followed by extracting with ethyl acetate. After removing water layer, an organic layer was washed with 10% K2CO3 aqueous solution and with saturated solution of sodium chloride, followed by drying with the use of magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure and 7.8 g of 4′-bromo-N-methyl-2′-amino-benzanilide was obtained as white solids (yield: 90%). The white solids were used in the next reaction as crude products.

Provenance & Evidence