Ammonium Chloride → HCID 58042501, compound

3-Chloro-2-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-5-nitropyridine (Preparation 51, 2.55 g, 7.9 mmol), ammonium chloride (2.50 g, 46.7 mmol) and iron powder (1.70 g, 30.4 mmol) were suspended in a mixture of ethanol (10 mL) and water (3 mL). The suspension was heated for 3 hours under reflux then allowed to cool to room temperature. The reaction mixture was filtered on a celite pad and washed with ethanol. The filtrate was concentrated in vacuo and the residue partitioned between water and EtOAc. The aqueous layer was further extracted with EtOAc (2×25 mL). The combined organics were dried over magnesium sulfate and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 50% diethyl ether in heptane to afford the title compound as a light yellow oil (2.0 g, 87%).

1. temperatureThe suspension was heated for 3 hours
2. temperatureunder reflux
3. filtrationThe reaction mixture was filtered on a celite pad
4. washwashed with ethanol
5. concentrationThe filtrate was concentrated in vacuo
6. customthe residue partitioned between water and EtOAc
7. extractionThe aqueous layer was further extracted with EtOAc (2×25 mL)
8. dry with materialThe combined organics were dried over magnesium sulfate
9. concentrationconcentrated in vacuo
10. customThe resulting crude was purified by silica gel chromatography
11. washeluting with 50% diethyl ether in heptane

ORD record

ord-13d2297eff68491c8a2ddee5dd3fc821

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2