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

HRID 466011노트

반응식

HRID 466011 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1118Sulfuric Acid촉매HCID 176Acetic Acid용매

반응 조건

온도
135 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-107a60501a1e4e338f58c4fd604a95cb
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05155114

반응 노트

불러오는 중…