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

HRID 461800노트

반응식

HRID 461800 반응식
[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]

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b29ce68f048c4efc93934a8bfe6d0558
출처 데이터셋
uspto-grants-1977_12
특허 번호
US04064251

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