Phosphorus oxychloride → 2-Chloro-4-methyl-nicotinonitrile

14 g (104 mmol) of 3-cyano-4-methylpyridone was slowly added to a mixture of 6.52 g (31.3 mmol) of phosphorus pentachloride and 30 ml (48 g, 313 mmol) of phosphorus oxychloride, followed by stirring at room temperature for 70 minutes and then under reflux with heating for 2 hours. After the reaction mixture was left to stand to cool, it was poured into ice water (400 ml) so that the surplus reagent was decomposed, followed by extraction with 100 ml of dichloromethane three times. The dichloromethane solution was washed with 100 ml of a saturated sodium chloride solution and dried over magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 15.1 g of crude crystals of 2-chloro-3-cyano-4-methylpyridine. 1H-NMR (400 MHz, DMSO-d6): δ(ppm) 2.86 (s, 3H), 7.89 (d, J=5.6 Hz, 1H), 8.86 (d, J=5.6 Hz, 1H)

1. temperatureunder reflux
2. temperaturewith heating for 2 hours
3. waitAfter the reaction mixture was left
4. temperatureto cool
5. extractionfollowed by extraction with 100 ml of dichloromethane three times
6. washThe dichloromethane solution was washed with 100 ml of a saturated sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. distillationthe solvent was distilled off under reduced pressure

ORD-Eintrag

ord-44ab420cf53447ba898ef6b171d73d4e

Quelldatensatz

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08653113B2