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

9.5 g (28 mmol) of 4′-bromo-N-methyl-2′-nitrobenzanilide was dissolved in 100 mL of tetrahydrofuran. A solution of 25 g (142 mmol) of sodium hydrosulfite in 90 mL of water was added to the solution while stirring the solution at room temperature in an argon atmosphere. After the addition of 10 mL of methanol, the mixture was stirred for 3 hours. After the addition of 100 mL of ethyl acetate, a solution of 12 g (142 mmol) of sodium hydrogencarbonate in 125 mL of water was added to the mixture. After stirring the mixture at room temperature for 1 hour, the mixture was extracted with ethyl acetate. After removing the aqueous phase, the organic phase was washed with a 10% potassium carbonate aqueous solution and a saturated sodium chloride solution, and dried over magnesium sulfate. After filtering the organic phase, the solvent was evaporated under reduced pressure to obtain 7.8 g of 4′-bromo-N-methyl-2′-aminobenzanilide as a white solid (yield: 90%).

1. stirringthe mixture was stirred for 3 hours
2. stirringAfter stirring the mixture at room temperature for 1 hour
3. extractionthe mixture was extracted with ethyl acetate
4. customAfter removing the aqueous phase
5. washthe organic phase was washed with a 10% potassium carbonate aqueous solution
6. dry with materiala saturated sodium chloride solution, and dried over magnesium sulfate
7. filtrationAfter filtering the organic phase
8. customthe solvent was evaporated under reduced pressure

ORD record

ord-8fb2cc6249a5481e92ebc8c20b10c827

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08803420B2