Water → HCID 22917216, compound

HRID 1973370Notes

Reaction equation

HRID 1973370 reaction equation
Cl[C:2]1[C:3]([C:14]([O:16]CC)=[O:15])=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([CH3:12])=[C:7]([CH3:13])[CH:6]=2.C(=O)([O-])[O-].[Ba+2].O.[H][H]>C(O)C.[Pd](Cl)Cl>[CH3:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][C:7]=1[CH3:13])[N:4]=[C:3]([C:14]([OH:16])=[O:15])[CH:2]=[N:11]2

Participants

7

Reactant 4

HCID 962WaterHCID 10563Barium CarbonateHCID 12283437HCID 12283437, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22917216HCID 22917216, compound

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 702EthanolSolvent

Procedure

3-Chloro-6,7-dimethyl-2-quinoxalinecarboxylic acid, ethyl ester (Example 14a) (6.0 g), palladium chloride (0.4 g) and barium carbonate (17.4 g) in ethanol (500 ml) containing water (6 ml) were stirred in an atmosphere of hydrogen at room temperature and atmospheric pressure for 18 hours. The mixture was filtered and the filtrate was evaporated. The residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°). The solid was dissolved in aqueous sodium hydroxide (20 ml., 2N) and ethanol (20 ml) and the solution was heated under reflux for 10 minutes and cooled. Hydrochloric acid was added and the solid was collected and crystallised from aqueous ethanol. It had m.p. 214.5°-216° (20%).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was crystallised from a mixture of ethyl acetate and light petroleum (b.p. 60°-80°)
  4. dissolutionThe solid was dissolved in aqueous sodium hydroxide (20 ml., 2N)
  5. temperatureethanol (20 ml) and the solution was heated
  6. temperatureunder reflux for 10 minutes
  7. temperaturecooled
  8. additionHydrochloric acid was added
  9. customthe solid was collected
  10. customcrystallised from aqueous ethanol

Sources & evidence

ORD record
ord-3e73a5f2533c4b9183636f56304be4b7
Source dataset
uspto-grants-1976_12
Patent number
US03997535

Reaction notes

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