Ethylene carbonate → HCID 18186792, compound

HRID 1296666Notes

Reaction equation

HRID 1296666 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.C1(=O)O[CH2:15][CH2:14][O:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([O:1][CH2:15][CH2:14][OH:13])[CH:11]=2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 7303Ethylene carbonateHCID 11430Potassium CarbonateHCID 4597677-Isoquinolinol

Product 1

HCID 18186792HCID 18186792, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 7-hydroxyisoquinoline (1.15 g, 7.9 mmol), ethylene carbonate (0.98 g, 11.1 mmol), powdered K2CO3 (0.65 g, 4.7 mmol) in dry DMF (20 mL) was stirred at 145° C. for two hours. The reaction was quenched with MeOH (1 mL), filtered and the solvent was removed under reduced pressure. The residue was taken up between alkaline water (K2CO3) and CHCl3. Concentration of the dried (MgSO4) organic phase afforded 1.4 g (94%) of the title compound as a yellow oil that solidified upon standing. Purity 91% (HPLC). Fragmenting mass analysis supports the stated structure.

Workup

  1. customThe reaction was quenched with MeOH (1 mL)
  2. filtrationfiltered
  3. customthe solvent was removed under reduced pressure
  4. dry with materialConcentration of the dried (MgSO4) organic phase

Sources & evidence

ORD record
ord-5b70df6f78004869915dfea8185abeb9
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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