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-eb7a2bce8c8c4576ab7c8290a8817029

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555557B1