Hydrazine → 2-Bromo-6-hydrazinopyridine

A mixture of 2,6-dibromopyridine (1.44 g, 6.1 mmol) and hydrazine (1.65 mL, 32.2 mmol) in butanol (100 mL) was stirred at reflux for 18 hours. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was partitioned between an aqueous saturated solution of sodium bicarbonate and EtOAc. The organic layer was separated and washed with brine, dried over Na2SO4, filtered and concentrated to give (6-Bromopyridin-2-yl)hydrazine as a white solid (1.0 g, 92%). 1H NMR (400 MHz, CHCl3-d): δ 7.36-7.28 (m, 1 H); 6.82 (d, J=7.70 Hz, 1 H); 6.67 (d, J=7.7 Hz, 1 H); 5.97 (s, 1 H); 3.80 (s, 2 H).

1. temperatureat reflux for 18 hours
2. concentrationconcentrated under reduced pressure
3. customThe residue was partitioned between an aqueous saturated solution of sodium bicarbonate and EtOAc
4. customThe organic layer was separated
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-dd25318a2da6447e895683bc128d27d0

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173650B2