4-Bromo-2-methyl-6-nitroaniline → 5-Bromo-3-methylbenzene-1,2-diamine

To a stirred solution of compound 4-bromo-2-methyl-6-nitroaniline (5.0 g) in EtOH (85 ml) and water (43 ml) were added iron powder (6.0 g) and CaCl2 (4.8 g) at room temperature and the resulting reaction mixture was then heated at reflux for 4 h. The mixture was then cooled to room temperature, filtered through Celite, and washed with EtOH. The filtrate was concentrated and the resulting residue was diluted with DCM. The DCM layer was successively washed with water and brine, dried over Na2SO4 and concentrated in vacuo to give the title compound (4.0 g) as a dark brown solid.

1. customthe resulting reaction mixture
2. temperaturewas then heated
3. temperatureat reflux for 4 h
4. filtrationfiltered through Celite
5. washwashed with EtOH
6. concentrationThe filtrate was concentrated
7. additionthe resulting residue was diluted with DCM
8. washThe DCM layer was successively washed with water and brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated in vacuo

ORD record

ord-759cdde3c0614094989b0f36d6833c41

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365540B2