Stannous Chloride → 5-Bromo-3-methylbenzene-1,2-diamine

To a suspension of 4-bromo-2-methyl-6-nitroaniline (2.0 g, 8.7 mmol) in EtOH (20 mL) was added SnCl2 (5.0 g, 26.1 mmol). The reaction mixture was heated at reflux for 14 h, cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc (100 mL) and partitioned between satd. aq. NaHCO3 solution (200 mL). The resulting slurry was filtered through a pad of Celite® and the wet cake was washed with EtOAc (3×50 mL). The filtrate was washed sequentially with satd. aq. NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 1.27 g (72%) of 5-bromo-3-methylbenzene-1,2-diamine (72) as yellow oil: MS (ESI) m/z=201.1 [M+1]+.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 14 h
3. concentrationconcentrated in vacuo
4. additionThe residue was diluted with EtOAc (100 mL)
5. custompartitioned between satd
6. filtrationThe resulting slurry was filtered through a pad of Celite®
7. washthe wet cake was washed with EtOAc (3×50 mL)
8. washThe filtrate was washed sequentially with satd
9. dry with materialaq. NaHCO3, water, and brine, dried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-89e1b6cb82544dd283e2b6c1fb9df1c8

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637537B2