Hydroxyamine hydrochloride → HCID 54190512, compound

HRID 2256903Notes

Reaction equation

HRID 2256903 reaction equation
C[N:2](C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])=[O:6].Cl.N[OH:23]>C(O)C>[OH:6][C:5]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][C:8]=2[N+:17]([O-:19])=[O:18])[O:23][N:2]=[CH:3][CH2:4]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 2740322HCID 2740322, compound

Product 1

HCID 54190512HCID 54190512, compoundYield 449%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-dimethylamino-1-(2-nitro-4-trifluoromethylphenyl)-prop-2-en-1-one (41.0 g) and hydroxylamine hydrochloride (1 1.9 g) in dry ethanol (280 ml) was stirred at room temperature overnight. It was evaporated to dryness and the residue was dissolved in a mixture of ether (150 ml) and water (100 ml). The layers were separated and the organic layer was washed with water (100 ml), dried (anhydrous sodium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was triturated with petroleum spirit (bp 60°-80° C.) (20 ml) and filtered to give 5-hydroxy-5-(2-nitro-4-trifluoromethylphenyl)-isoxazoline (33.9 g) as a pale yellow solid mp 122°-123° C.

Workup

  1. customIt was evaporated to dryness
  2. dissolutionthe residue was dissolved in a mixture of ether (150 ml) and water (100 ml)
  3. customThe layers were separated
  4. washthe organic layer was washed with water (100 ml)
  5. dry with materialdried (anhydrous sodium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was triturated with petroleum spirit (bp 60°-80° C.) (20 ml)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-118c5238719e45f79effe06c5a8a4950
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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