Hydroxyamine hydrochloride → 3-(3-Bromophenyl)isoxazol-5-amine

HRID 70295Notes

Reaction equation

HRID 70295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][C:10]#[N:11])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:14][OH:15].CC([O-])=O.[Na+]>CCO.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[C:10]([NH2:11])[O:15][N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 27568393-(3-Bromophenyl)-3-oxopropanenitrile

Product 1

HCID 185260763-(3-Bromophenyl)isoxazol-5-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-(3-bromophenyl)-3-oxopropanenitrile (1.12 g; 5.00 mmol; Note 1) in EtOH (20 mL) was added a solution of hydroxylamine hydrochloride (1.74 g; 25 mmol) and NaOAc (2.46 g; 30 mmol) in water (20 mL). The mixture was heated under reflux for 1 h, cooled and concentrated in vacuo. The residue was slurried in 1N NaOH and extracted with Et2O (×1). The organic layer was washed (water, brine), dried over Na2SO4 and concentrated in vacuo affording the title compound as a pale yellow solid which was used without further purification. LC/MS (method B) 2.21 min, m/z 239, 241 (Br isotopes).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. extractionextracted with Et2O (×1)
  6. washThe organic layer was washed (water, brine)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c39b54f1fa1b4954b6e76d35b6f8f2a0
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Reaction notes

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