Hydroxyamine hydrochloride → HCID 430947, compound

HRID 1604989Notes

Reaction equation

HRID 1604989 reaction equation
[Na].Cl.[NH2:3]O.[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7]([CH2:14][C:15](Cl)=[N:16][OH:17])=[N:6]1>C(O)C>[O:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7]([CH2:14][C:15](=[N:16][OH:17])[NH2:3])=[N:6]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 5360545SodiumHCID 85444374HCID 85444374, compound

Product 1

HCID 430947HCID 430947, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In ethanol (10 ml) was dissolved metal sodium (0.4 g) and thereto was further added hydroxylamine hydrochloride (0.8 g). To the solution was added a solution of 1,2-benzisoxazole-3-acetohydroximic chloride (5.0 g) in ethanol (40 ml) under ice-cooling and the mixture was stirred for hour. The mixture was distilled under a reduced pressure to remove the solvent. To the residue was added chloroform and the insoluble substance was filtered off, and the filtrate was subjected to silica gel column chromatography and eluted with 5 % methanol-chloroform. The resulting precipitated crystallines were separated by filtration and recrystallized from ethanol to give the desired compound (1.0 g). m.p. 161° to 163°C.

Workup

  1. temperaturecooling
  2. distillationThe mixture was distilled under a reduced pressure
  3. customto remove the solvent
  4. additionTo the residue was added chloroform
  5. filtrationthe insoluble substance was filtered off
  6. washeluted with 5 % methanol-chloroform
  7. customThe resulting precipitated crystallines
  8. customwere separated by filtration
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c6ba0d3ebef544199c0ca631e29dbaea
Source dataset
uspto-grants-1976_04
Patent number
US03948928

Reaction notes

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