Quinoline → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Temperatur

100 °C

To a solution of phosphoryl chloride (2.0 mL, 21.2 mmol) and quinoline (1.30 mL, 10.8 mmol) was added solid powder 3-nitro-5-(trifluoromethyl)pyridin-2-ol (4.00 g, 18.3 mmol) (95% purity). The resulting dark brown thick suspension was heated to reflux for 4 h and gradually turned into a very cloudy dark brown solution. After cooling to 100° C., water (11 mL) was slowly added to the mixture which was further cooled to room temperature and neutralized carefully with Na2CO3. The resulting solution was extracted with EtOAc three times. The extracts were combined, dried over MgSO4, filtered, and evaporated in vacuo. The residue was purified by flash chromatography on silica gel (EtOAc/hexanes 30:70) to afford 2.28 g of desired product.

1. temperatureThe resulting dark brown thick suspension was heated
2. temperatureto reflux for 4 h
3. extractionThe resulting solution was extracted with EtOAc three times
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated in vacuo
7. customThe residue was purified by flash chromatography on silica gel (EtOAc/hexanes 30:70)

ORD-Eintrag

ord-1166b3494f0f4aeb967b7d823ee371ed

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07449467B2