Hydroxyamine hydrochloride → 2-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde oxime

HRID 604085Notes

Reaction equation

HRID 604085 reaction equation
[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][CH3:20])[C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=2[CH:8]=O)[CH2:3][CH2:2]1.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>C(O)C>[CH:1]1([CH2:4][N:5]([CH2:18][CH2:19][CH3:20])[C:6]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=2[CH:8]=[N:22][OH:23])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866267692-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde

Product 1

HCID 866268392-(Cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde oximeYield 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (30 ml) are added 2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde (6.8 g), hydroxylamine hydrochloride (1.66 g) and sodium acetate (1.95 g) and the mixture is stirred at room temperature overnight. Ethanol is removed by evaporating under reduced pressure and thereto is added chloroform and water, and the mixture is separated. The organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1→2:1) to give 2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzaldehyde oxime (5.78 g). MS (m/z): 301 [M+H]+

Workup

  1. customEthanol is removed
  2. customby evaporating under reduced pressure
  3. additionis added chloroform and water
  4. customthe mixture is separated
  5. washThe organic layer is washed with a saturated brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1→2:1)

Sources & evidence

ORD record
ord-01fe7a08450d465594e83a1a07750c00
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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