Hydrochloric Acid → 1-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

To a mixture of 2-(2-fluoropyridin-4-yl)-1-(3-trifluoromethylphenyl)ethanone (10.80 g, 0.038 mol) in ethanol (200 mL), at −10° C., under argon, was added tert-butyl nitrite (5.0 mL, 0.042 mol) and hydrogen chloride (12.2 mL, 2.5M in ethanol, 0.031 mol) dropwise while maintaining the temperature below −5° C. Upon completion of addition, the reaction was allowed to warm to RT for 2 hrs. The reaction mixture was then concentrated in vacuo, diluted with water (100 mL), basified with saturated sodium bicarbonate (200 ml), and extracted with ethyl acetate (3×400 mL). The combined organic layers were washed with water (300 mL), dried with brine (300 mL) and anhydrous sodium sulfate, filtered and concentrated to yield 11.4 g of the title compound, as an oil.

1. temperaturewhile maintaining the temperature below −5° C
2. additionUpon completion of addition
3. concentrationThe reaction mixture was then concentrated in vacuo
4. additiondiluted with water (100 mL)
5. extractionextracted with ethyl acetate (3×400 mL)
6. washThe combined organic layers were washed with water (300 mL)
7. dry with materialdried with brine (300 mL) and anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated

ORD-Eintrag

ord-d0751a2f8cd0480680bec22df0e7874c

Quelldatensatz

uspto-grants-2001_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06291457B1