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-189aecee7adf4dd497b7cc805ecd4484

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2