Aluminum(III) Chloride → 4-Amino-6-chloropyridin-2(1H)-one

2-Chloro-6-ethoxypyridin-4-amine (10.0 g, prepared according to the reported preparation in J. Med. Chem., (2006), 49 (12), 3563-3580) and aluminum trichloride (19.3 g) were suspended in toluene (300 mL) and heated at reflux under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and partitioned between saturated aqueous Rochelle's salt and ethyl acetate and vigorously stirred overnight. The biphasic mixture was filtered. The aqueous was repeatedly extracted with ethyl acetate. The combined organics were dried, magnesium sulfate and concentrated under reduced pressure to furnish the title compound (4.23 g), which was used without further purification, possessing the following physical data.

1. customaccording to the reported preparation in J
2. temperatureheated
3. temperatureat reflux under a nitrogen atmosphere
4. custompartitioned between saturated aqueous Rochelle's salt and ethyl acetate and vigorously stirred overnight
5. filtrationThe biphasic mixture was filtered
6. extractionThe aqueous was repeatedly extracted with ethyl acetate
7. customThe combined organics were dried
8. concentrationmagnesium sulfate and concentrated under reduced pressure

ORD record

ord-03b3171d315e40a0abfea0d6cd2f73d6

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809538B2