Sodium Hydroxide → 5-Amino-3-phenylisoxazole

HRID 2263065Notes

Reaction equation

HRID 2263065 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][C:4]#[N:5].S(O)(O)(=O)=O.[NH2:17][OH:18].[OH-].[Na+]>C(O)C>[C:6]1([C:2]2[CH:3]=[C:4]([NH2:5])[O:18][N:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 64799BenzoylacetonitrileHCID 159255Hydroxylamine, sulfate (1:1)

Product 1

HCID 2612015-Amino-3-phenylisoxazoleYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-oxo-3-phenylpropanenitrile (5.00 g, 34.4 mmol), hydroxylamine sulfate (3.10 g, 18.9 mmol), ethanol (35 ml) and an aqueous solution (35 ml) of sodium hydroxide (1.66 g, 41.4 mmol) was stirred at 80° C. for 24 hours. After cooling to room temperature, the reaction mixture was adjusted to pH=11 by addition of an aqueous 8N sodium hydroxide solution and then extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the desired product (1.09 g, 19.8%) as a solid.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a311874d0a10431b84af4f7e15a5bd58
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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