Sulfuric Acid → 5-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

HRID 1703541Notes

Reaction equation

HRID 1703541 reaction equation
[C:1]1([C:7]2[C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([CH2:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)=O)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:15][N:14]1[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]=2[C:12]1=[O:13]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 227620923-phenyl-5-(2-pyridylcarbonylmethyl)-N-methyl-isoxazole-4-carboxamide

Product 1

HCID 221377335-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4(5H)-one

Procedure

A mixture of 20.1 g. (0.0627 mole) of 3-phenyl-5-(2-pyridylcarbonylmethyl)-N-methyl-isoxazole-4-carboxamide and 200 ml. of 2M sulfuric acid is refluxed for 24 hours. The mixture is cooled and made basic with 2N sodium hydroxide and then extracted with methylene chloride. The methylene chloride layer is washed with water, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The resulting solid is purified by column chromatography to give 5-methyl-3-phenyl-6-(2-pyridyl)-isoxazolo[4,5-c]pyridin-4-(5H)-one; m.p. 160° to 162° C.

Workup

  1. additionA mixture of 20.1 g
  2. temperatureThe mixture is cooled
  3. extractionextracted with methylene chloride
  4. washThe methylene chloride layer is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting solid is purified by column chromatography

Sources & evidence

ORD record
ord-22f53045f1154193bd841f06a7d87408
Source dataset
uspto-grants-1978_11
Patent number
US04124714

Reaction notes

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