Hydroxyamine hydrochloride → 5-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde oxime

HRID 1506305Notes

Reaction equation

HRID 1506305 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]=O)[C:8]=2[C:14]([F:17])([F:16])[F:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20].C([O-])(=O)C.[Na+]>CO>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH:12]=[N:19][OH:20])[C:8]=2[C:14]([F:17])([F:16])[F:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866698695-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde

Product 1

HCID 1363502905-Phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde oximeYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde (step B, 0.415 g, 1.721 mmol), hydroxylamine hydrochloride (0.179 g, 2.58 mmol), and sodium acetate (0.212 g, 2.58 mmol) in methanol (5 mL) was heated at reflux for 45 min. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in water (10 mL), and the solid was collected by vacuum filtration, washed with water (2×5 mL), and dried overnight under reduced pressure to give 5-phenyl-4-(trifluoromethyl)isoxazole-3-carbaldehyde oxime (0.360 g, 1.41 mmol, 82% yield). The compound had an HPLC ret. time=2.43 min. (condition A); LC/MS M+1=256.9.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 45 min
  3. concentrationconcentrated under reduced pressure
  4. filtrationthe solid was collected by vacuum filtration
  5. washwashed with water (2×5 mL)
  6. customdried overnight under reduced pressure

Sources & evidence

ORD record
ord-ce3917288f124d24a23f86fbdc8e7783
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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