Hydroxyamine hydrochloride → HCID 20297499, compound

HRID 1389016Notes

Reaction equation

HRID 1389016 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([C:9](=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[CH:5]OCC.C([O-])(=O)C.[Na+].Cl.[NH2:28]O>C(O)C>[CH3:1][O:2][C:3]([C:4]1[CH:5]=[N:28][O:20][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)=[O:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 54239560HCID 54239560, compound

Product 1

HCID 20297499HCID 20297499, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of methyl-2-(3'-trifluoromethylbenzoyl)-3-ethoxypropenoate (8.55 g.; 0.028 mol.) in 60 ml. of ethanol and anhydrous sodium acetate (2.5 g.; 0.03 mol.) was treated with hydroxylamine hydrochloride (2.1 g.; 0.03 mol.). The mixture was heated at reflux for 2 hours, cooled to 25° C., and then poured onto 50 g. of ice. The resulting liquid was extracted five times with 40 ml. of methylene chloride. The organic layer was washed with water, sodium bicarbonate, water, dried over sodium sulfate, filtered and concentrated to yield methyl-5-(3'-trifluoromethylphenyl)-4-isoxazolecarboxylate as an orange oil.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. additionpoured onto 50 g
  4. extractionThe resulting liquid was extracted five times with 40 ml
  5. washThe organic layer was washed with water, sodium bicarbonate, water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-fed624b7cb9741db8b66182b7b8eeba5
Source dataset
uspto-grants-1981_01
Patent number
US04243406

Reaction notes

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