Sodium Bicarbonate → 3-(2-Oxo-1,2,5,6-tetrahydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 466011ノート

反応式

HRID 466011 の反応式
[C:1]1([C:7]2[CH:15]=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][C:17]1=[O:23].C(=O)([O-])O.[Na+]>S(=O)(=O)(O)O.C(O)(=O)C>[O:23]=[C:17]1[CH:18]=[C:19]([C:15]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=23)[CH2:20][CH2:21][NH:16]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 108878632,4-PiperidinedioneHCID 156203422-Phenylpyrazolo[1,5-a]pyridine

生成物 1

HCID 151581103-(2-Oxo-1,2,5,6-tetrahydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine

試薬・触媒・溶媒 2

HCID 1118Sulfuric Acid触媒HCID 176Acetic Acid溶媒

反応条件

温度
135 °C

実験手順

A mixture of 2-phenylpyrazolo[1,5-a]pyridine (0.50 g, 2,4-piperidinedione (0.292 g), concentrated sulfuric acid (1 drop) and acetic acid (0.5 ml) was heated at 135° C. for 13.5 hours. A saturated aqueous solution of sodium hydrogen carbonate (20 ml) was added to the reaction mixture and the mixture was extracted with chloroform (20 ml×2). The combined extract was washed with a saturated aqueous solution of sodium chloride (20 ml) and dried over magnesium sulfate. The solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and ethyl acetate (9:1) and recrystallized from ethyl acetate to give crystals of 3-(2-oxo-1,2,5,6-tetrahydropyridin-4-yl)-2-phenylpyrazolo[1,5-a]pyridine.

後処理

  1. extractionthe mixture was extracted with chloroform (20 ml×2)
  2. extractionThe combined extract
  3. washwas washed with a saturated aqueous solution of sodium chloride (20 ml)
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel using
  7. additiona mixture of chloroform and ethyl acetate (9:1)
  8. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-107a60501a1e4e338f58c4fd604a95cb
出典データセット
uspto-grants-1992_10
特許番号
US05155114

反応ノート

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