Sulfuric Acid → 5-methyl-3-phenyl-6-(p-tolyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

HRID 2072199Notes

Reaction equation

HRID 2072199 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:7][O:8][C:9]=1[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[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][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:10][C:9]2[O:8][N:7]=[C:6]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:5]=2[C:3]1=[O:4]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 20305048N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide

Product 1

HCID 220155675-methyl-3-phenyl-6-(p-tolyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

Procedure

A mixture of 26.1 g. (0.0815 mole) of N-methyl-5-(4-methylphenacyl)-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-phenyl-6-(p-tolyl)-isoxazolo [4,5-c]pyridin-4(5H)-one; m.p. 155° to 156° 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-eb4cf92e874f4d328637cf8fd2ab4a3e
Source dataset
uspto-grants-1977_09
Patent number
US04049813

Reaction notes

Loading…