2-Bromo-5-methyl-3-nitropyridine → 2-Bromo-5-methylpyridin-3-amine

Temperature

80 °C

To Fe power (2.18 g, 39.0 mmol), AcOH (10 mL) was added drop wise and heated to 80° C. To it, a solution of 2-bromo-5-methyl-3-nitro-pyridine (1.96 g, 9.07 mmol) in AcOH (10 mL) was added slowly. After 30 min, reaction mixture was allowed to cool to room temperature and diluted with EtOAc (25 mL), filtered through a pad of celite. The filter cake was washed with EtOAc (25 mL) and filterate was concentrated. The residual liquid was slowly treated with saturated aqueous NaHCO3 solution (70 mL), followed by small portions of solid NaHCO3 to neutralize the AcOH, extracted with EtOAc (2×50 mL) and the extracts were dried (anhydrous Na2SO4) and concentrated under reduced pressure to get 2-bromo-5-methyl-pyridin-3-ylamine (1.45 g) as a brown solid in 86.3% yield. ESMS m/z (relative intensity): 187 (M+H)+ (100).

1. customreaction mixture
2. temperatureto cool to room temperature
3. filtrationfiltered through a pad of celite
4. washThe filter cake was washed with EtOAc (25 mL) and filterate
5. concentrationwas concentrated
6. additionThe residual liquid was slowly treated with saturated aqueous NaHCO3 solution (70 mL)
7. extractionextracted with EtOAc (2×50 mL)
8. dry with materialthe extracts were dried (anhydrous Na2SO4)
9. concentrationconcentrated under reduced pressure

ORD record

ord-f322b3a0bf2e4167843354e460d0ad63

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519135B2