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

HRID 1470675Notes

Reaction equation

HRID 1470675 reaction equation
[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

Participants

4

Reactant 2

HCID 1049PyridineHCID 10752Coumarin-3-Carboxylic Acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a1ac96e6d7ea4d16b51d03c8e1763667
Source dataset
uspto-grants-2015_04
Patent number
US09006466B2

Reaction notes

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