Hydrazine hydrate (1:1) → 1-(5-Bromo-4-methylpyridin-2-YL)hydrazine

Temperature

120 °C

Combined 5-bromo-2-chloro-4-methylpyridine (15.0 g, 72.46 mmol) and EtOH (60 mL) and added hydrazine hydrate (85%, 45 mL) and stirred at 120° C. overnight. The reaction mixture was concentrated to give a residue which was extracted with EtOAc (50 mL×2) and water (50 mL×2). Then combined organic layers were extracted with brine, dried over Na2SO4 to and concentrated to give a residue which was purified by flash chromatography (petroleum ether: EtOAc=10:1 to 1:5) to give the title compound (7.8 g, 53%).

1. concentrationThe reaction mixture was concentrated
2. customto give a residue which
3. extractionwas extracted with EtOAc (50 mL×2) and water (50 mL×2)
4. extractionThen combined organic layers were extracted with brine
5. dry with materialdried over Na2SO4 to and
6. concentrationconcentrated
7. customto give a residue which
8. customwas purified by flash chromatography (petroleum ether: EtOAc=10:1 to 1:5)

ORD record

ord-b607b20b44504d0c9ea7dd17e0e16a6d

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09345713B2