3-phenyl-5-(4-methyl-beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide → N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide

HRID 2083787Notes

Reaction equation

HRID 2083787 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][CH:17]([OH:25])[C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH3:15][NH:14][C:12]([C:11]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][O:9][C:10]=1[CH2:16][C:17]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1)=[O:25])=[O:13]

Participants

4

Reactant 2

HCID 203050573-phenyl-5-(4-methyl-beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamideHCID 131709961Jones' reagent

Product 1

HCID 20305048N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 41.4 g. (0.123 mole) of 3-phenyl-5-(4-methyl-β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide and 800 ml. of acetone is treated dropwise with the addition of 92.5 ml. (0.185 mole) of Jones reagent [100 g. chromium trioxide, 160 ml. concentrated sulfuric acid with water to 500 ml.] and the resulting mixture is stirred at room temperature for 2 hours. The supernatant liquid is decanted and the solvent removed in vacuo, the residue is taken up in water/methylene chloride and the layers separated. The organic phase is washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is treated with ether to give a solid and then triturated with ethanol to give N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide.

Workup

  1. additionA mixture of 41.4 g
  2. customThe supernatant liquid is decanted
  3. customthe solvent removed in vacuo
  4. customthe layers separated
  5. washThe organic phase is washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. additionThe residue is treated with ether
  10. customto give a solid
  11. customtriturated with ethanol

Sources & evidence

ORD record
ord-734a3875c2ab49a99454de18223f5b00
Source dataset
uspto-grants-1978_04
Patent number
US04086421

Reaction notes

Loading…