Methylhydrazine → 2-Bromo-6-(1-methylhydrazinyl)pyridine

Temperature

100 °C

A suspension of 2,6-dibromopyridine (10.0 g, 42.0 mmol) in anhydrous methylhydrazine (10 mL) was heated at 100° C. for 2 h. The mixture was cooled to room temperature and washed with water (3×20 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica gel, hexanes/EtOAc, 80:20) gave the title compound (5.70 g, 66%) as white solid: 1H NMR (500 MHz, CDCl3) δ 7.30-7.26 (dd, J=8.5, 7.8Hz, 1H), 6.83 (d, J=8.0 Hz, 1H), 6.73 (d, J=7.0 Hz, 1H), 4.03 (br s, 2H), 3.36 (s, 3H).

1. temperatureThe mixture was cooled to room temperature
2. washwashed with water (3×20 mL)
3. customThe organic layer was separated
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customPurification by flash column chromatography (silica gel, hexanes/EtOAc, 80:20)

ORD record

ord-346deb181069402a8d0b06398a8a7ab6

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073925B2