Hydroxylamine → HCID 136444127, compound

HRID 1755987Notes

Reaction equation

HRID 1755987 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][N:5]=1)(=O)[CH3:2].[NH2:14][OH:15].C([O-])(=O)C.[Na+].O>C(O)C>[C:1](=[N:14]/[OH:15])(\[C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][N:5]=1)/[CH3:2]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 962Water2×HCID 517045Sodium AcetateHCID 103301301-[4-(Trifluoromethyl)pyridin-2-yl]ethanone

Product 1

HCID 136444127HCID 136444127, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-acetyl-4-trifluoromethylpyridine (1.2 g), hydroxylamine (0.495 g) and sodium acetate (2.2 g) in a mixture of ethanol:water (20:10 ml) was heated under reflux for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate (×2). The combined extracts were washed with water, dried and concentrated to give a solid which was washed with hexane to give (E)-2-acetyl-4-trifluoromethylpyridine oxime (1.0 g, 77% yield) as a pale pink solid; 1H NMR (270 MHz): δ2.39(3H,s), 7.47(1H,d), 7.89(1H,brs), 8.12(1H,s), 8.12(1H,s), 8.78(1H,d); ppm.

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined extracts were washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto give a solid which
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-6b0187027a0246a8a195489cbe853e8c
Source dataset
uspto-grants-1995_08
Patent number
US05439910

Reaction notes

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