Pyridine → isoquinolin-1-yl 2-oxo-2H-1-benzopyran-3-carboxylate

HRID 1470675노트

반응식

HRID 1470675 반응식
[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[O:3]1.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>S(Cl)(Cl)=O>[O:1]=[C:2]1[C:7]([C:8]([O:10][C:16]2[C:17]3[C:18](=[CH:14][CH:4]=[CH:5][CH:6]=3)[CH:19]=[CH:20][N:15]=2)=[O:9])=[CH:6][C:5]2[CH:11]=[CH:12][CH:13]=[CH:14][C:4]=2[O:3]1

참가 물질

4

반응물 2

HCID 1049PyridineHCID 10752Coumarin-3-Carboxylic Acid

생성물 1

HCID 71502783isoquinolin-1-yl 2-oxo-2H-1-benzopyran-3-carboxylate

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

1.0 g of the commercially available 2-oxo-2H-1-benzopyran-3-carboxylic acid and 10 ml of thionyl chloride were refluxed for 3 h. The resulting solution was evaporated under reduced pressure. The residue was suspended in 10 ml anhydrous toluene. The solvent was eliminated by distillation under reduced pressure. The two last steps were repeated twice. The residue was dispersed in 10 ml dioxane. To this suspension were added 1-hydroxyquinoleine (1.1 éq.) and anhydrous pyridine (1.1 eq.). After 90 min stirring at room temperature, the solvent was removed by distillation under reduced pressure. The residue was solubilized in chloroform and the organic phase was washed three times with HCl 0.1N, then dried over MgSO4. The solvent was evaporated under reduced pressure and the residue obtained was recrystallized in ethyl acetate.

후처리

  1. customThe resulting solution was evaporated under reduced pressure
  2. distillationThe solvent was eliminated by distillation under reduced pressure
  3. additionThe residue was dispersed in 10 ml dioxane
  4. customthe solvent was removed by distillation under reduced pressure
  5. washthe organic phase was washed three times with HCl 0.1N
  6. dry with materialdried over MgSO4
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue obtained
  9. customwas recrystallized in ethyl acetate

출처 및 근거

ORD 기록
ord-a1ac96e6d7ea4d16b51d03c8e1763667
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006466B2

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