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

HRID 862208Notes

Reaction equation

HRID 862208 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.C([O:25][N:26]=O)(C)(C)C.Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8](=[N:26][OH:25])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 119771402-(2-Fluoropyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]ethanone

Product 1

HCID 1363810621-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-(2-fluoropyridin-4-yl)-1-(3-trifluoromethylphenyl)ethanone (10.80 g, 0.038 mole) in ethanol (200 mL), at -10° C., under argon, was added tert-butylnitrite (5.0 mL, 0.042 mol) followed by hydrogen chloride (12.2 mL, 2.5M in ethanol, 0.031 mole) dropwise while maintaining the temperature below -5° C. Upon completion of addition, the reaction was allowed to warm to room temperature for 2 hours. The reaction was concentrated in vacuo, diluted with water (100 mL), basified with saturated sodium bicarbonate (200ml). This mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL). The organic layers were combined, washed with water (300 mL), washed with brine (300 mL), dried over anhydrous sodium sulfate, filtered and concentrated to an oil (11.4 g).

Workup

  1. temperaturewhile maintaining the temperature below -5° C
  2. additionUpon completion of addition
  3. concentrationThe reaction was concentrated in vacuo
  4. additiondiluted with water (100 mL)
  5. extractionThis mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL)
  6. washwashed with water (300 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil (11.4 g)

Sources & evidence

ORD record
ord-6abde5afbf754b80b3a5c907489def6a
Source dataset
uspto-grants-1998_02
Patent number
US05717100

Reaction notes

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