Sulfuric Acid → 5-methyl-3,6-diphenylisoxazolo[4,5-c]pyridin-4(5H)-one

HRID 1112379Notes

Reaction equation

HRID 1112379 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:7][O:8][C:9]=1[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)=[O:4].S(=O)(=O)(O)O>>[CH3:1][N:2]1[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:9]2[O:8][N:7]=[C:6]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]=2[C:3]1=[O:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 20304991N-methyl-5-phenacyl-3-phenyl-4isoxazole carboxamide

Product 1

HCID 42509095-methyl-3,6-diphenylisoxazolo[4,5-c]pyridin-4(5H)-one

Procedure

A mixture of 26.1 g. (0.0815 mole) of N-methyl-5-phenacyl-3-phenyl-4-isoxazole carboxamide and 261 ml. of 2M sulfuric acid is refluxed for 24 hours. The mixture is cooled and extracted with methylene chloride. The methylene chloride layer is washed with water and then brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is triturated with ether and then recrystallized from ethanol to give 5-methyl-3,6-diphenyl-isoxazolo[4,5-c]pyridin-4(5H)-one, m.p. 149°-151.5° C.

Workup

  1. additionA mixture of 26.1 g
  2. temperatureThe mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer is washed with water
  5. dry with materialbrine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue is triturated with ether
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-eb7023f1b66441858f97406583464ba5
Source dataset
uspto-grants-1978_10
Patent number
US04122182

Reaction notes

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