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

HRID 973033Notes

Reaction equation

HRID 973033 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 20304991HCID 20304991, compound

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-b1e45dbe111341eca5fc860bdf645e00
Source dataset
uspto-grants-1977_10
Patent number
US04054653

Reaction notes

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