Ammonium Chloride → Benzenamine, 3-bromo-4-methyl-

To a suspension of iron (1.5 g, 27.6 mmol) and ammonium chloride (2.46 g, 46 mmol) in water (50 mL) was slowly added a solution of 3-bromo-4-methyl-1-nitrobenzene (1.0 g, 4.6 mmol) in methanol (25 mL). The resulting mixture was refluxed for 2 hours. The solids formed were filtered through celite while the reaction mixture was still hot, the solvent of the clear filtrate was then removed. The crude residue was redissolved in water, extracted with ethyl acetate and dried over anhydrous sodium sulfate. The crude oil was adsorbed on silica gel and purified by flash chromatography on silica gel (hexanes/EtOAc from 95:5 to 50:50). The product, 3-bromo-4-methylaniline, was isolated as pale red oil (462 mg). HPLC Rt 3.425 minutes.

1. temperatureThe resulting mixture was refluxed for 2 hours
2. customThe solids formed
3. filtrationwere filtered through celite while the reaction mixture
4. customthe solvent of the clear filtrate was then removed
5. dissolutionThe crude residue was redissolved in water
6. extractionextracted with ethyl acetate
7. dry with materialdried over anhydrous sodium sulfate
8. custompurified by flash chromatography on silica gel (hexanes/EtOAc from 95:5 to 50:50)

ORD record

ord-cd23d8cbef744e02b4ad6354a2d7cbae

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304071B2