Ammonium Chloride → HCID 58042501, compound

3-Chloro-2-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-5-nitropyridine (Preparation 255, 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 the pad was washed with ethanol. The filtrate was concentrated in vacuo and the crude residue was partitioned between water and ethyl acetate. The aqueous layer was separated and extracted by ethyl acetate (2×25 mL). Organic layers were combined, dried over magnesium sulfate and concentrated in vacuo. The crude residue 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. washthe pad was washed with ethanol
5. concentrationThe filtrate was concentrated in vacuo
6. customthe crude residue was partitioned between water and ethyl acetate
7. customThe aqueous layer was separated
8. extractionextracted by ethyl acetate (2×25 mL)
9. dry with materialdried over magnesium sulfate
10. concentrationconcentrated in vacuo
11. customThe crude residue was purified by silica gel chromatography
12. washeluting with 50% diethyl ether in heptane

ORD record

ord-d44cfba622b140ea9fbbcd5e2e5deab8

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2