Hydroxyamine hydrochloride → Trifluoromethyl(3,4-methylenedioxyphenyl)methanone-oxime

HRID 580546Notes

Reaction equation

HRID 580546 reaction equation
[F:1][C:2]([C:5]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)=O)([F:4])[F:3].Cl.[NH2:17][OH:18].C([O-])(=O)C.[Na+]>CO.O>[F:1][C:2]([C:5]([C:7]1[CH:12]=[CH:11][C:10]2[O:13][CH2:14][O:15][C:9]=2[CH:8]=1)=[N:17][OH:18])([F:4])[F:3]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 108464551-(1,3-Benzodioxol-5-YL)-2,2,2-trifluoro-ethanone

Product 1

HCID 72726727Trifluoromethyl(3,4-methylenedioxyphenyl)methanone-oximeYield 76.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Trifluoromethyl(3,4-methylenedioxyphenyl) methanone (1.46 g, 0.0067 mole), hydroxylamine hydrochloride (1.06 g), 0.015 mole) and sodium acetate (0.86 g, 0.010 mole) were dissolved in a mixture of methanol (4 ml) and water (4 ml) and heated to reflux for 4.5 hours. After cooling to room temperature, water (10 ml) was added and the mixture extracted with ether (3×15 ml). The combined extracts were washed with water (20 ml) and brine (20 ml) and dried over anhydrous sodium sulfate. After filtration and removal of the solvent in vacuo the residue was recrystallized from a mixture of dichloromethane and petroleum spirit (40°-60° C.) to give trifluoromethyl(3,4-methylenedioxyphenyl)methanone-oxime (1.2 g), (76.9%) m.p. 96.0° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4.5 hours
  3. extractionthe mixture extracted with ether (3×15 ml)
  4. washThe combined extracts were washed with water (20 ml) and brine (20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration and removal of the solvent in vacuo the residue
  7. customwas recrystallized from a mixture of dichloromethane and petroleum spirit (40°-60° C.)

Sources & evidence

ORD record
ord-c3624a3e22724cd0909943c201dae39e
Source dataset
uspto-grants-1988_06
Patent number
US04753960

Reaction notes

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