Ammonia → 4-Methyl-3-cyanopyridine

3-Bromo-4-methylpyridine (20.0 g, 116 mmol) is dissolved in DMF (100 ml), and thereto is added cuprous cyanide (11.6 g, 30 mmol), and the mixture is heated under reflux for 18 hours. After cooling, a 25% aqueous ammonia (200 ml) and a saturated aqueous ammonium chloride solution (200 ml) are added to the reaction solution, and the mixture is extracted with ethyl acetate (200 ml×5). The organic layer is washed with a saturated brine (100 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give the title compound (11.0 g) as colorless crystals, m.p. 75-78° C.

1. temperaturethe mixture is heated
2. temperatureunder reflux for 18 hours
3. temperatureAfter cooling
4. extractionthe mixture is extracted with ethyl acetate (200 ml×5)
5. washThe organic layer is washed with a saturated brine (100 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD record

ord-4ad2b2ca584d42539bf977bdd3ee0cff

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06765095B2