Hydroxyamine hydrochloride → HCID 18996941, compound

HRID 374412Notes

Reaction equation

HRID 374412 reaction equation
Cl.NO.[CH:4]1([C:7](=[O:23])[C:8](=[CH:19][N:20](C)C)[C:9]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)=[O:10])[CH2:6][CH2:5]1>C(O)C>[CH:4]1([C:7]2[O:23][N:20]=[CH:19][C:8]=2[C:9]([C:11]2[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=2)=[O:10])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 53733250HCID 53733250, compound

Product 1

HCID 18996941HCID 18996941, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of hydroxylamine hydrochloride (0.4 g) and 3-cyclopropyl-1-(3,5-dichloropyridin-2-yl)-2-(dimethyl amino)methylenepropan-1,3-dione (1.68 g) in ethanol was stirred at room temperature overnight. The solvent was removed by evaporation and the residue was dissolved in dichloromethane. The resulting solution was washed with water, dried (anhydrous magnesium sulphate), filtered and evaporated. The residue was purified by column chromatography on silica eluted with a mixture of ethyl acetate and hexane to yield 5-cyclopropyl-4-(3,5-dichloropyridin-2-oyl)isoxazole (compound 1, 0.38 g) as a white solid, m.p. 81.9°-83.1° C.

Workup

  1. customThe solvent was removed by evaporation
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe resulting solution was washed with water
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica
  8. washeluted with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c3c37a3fb62d4ab58654fa26e2863a9b
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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