Sodium Acetate → Ethyl 4-hydroxy-5-methylquinoline-3-carboxylate

HRID 1915447Notes

Reaction equation

HRID 1915447 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]2[C:11]=1[NH:10][CH:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]2=[O:17].C([O-])(=O)C.[Na+]>[Pd]>[CH3:18][C:5]1[CH:4]=[CH:3][CH:2]=[C:11]2[C:6]=1[C:7](=[O:17])[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][NH:10]2

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 59410078ethyl 8-bromo-5-methyl-4-oxo-1H-quinoline-3-carboxylate

Product 1

HCID 21829729Ethyl 4-hydroxy-5-methylquinoline-3-carboxylateYield 22%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A flask charged with ethyl 8-bromo-5-methyl-4-oxo-1H-quinoline-3-carboxylate (895 mg, 2.89 mmol), sodium acetate (237 mg, 2.89 mmol) and Pd/C (180 mg, 1.69 mmol) was flushed under a N2 followed by evacuating under vacuum. Acetic acid (21 mL) was added under an inert atmosphere followed by evacuating under vacuum. The reaction was then stirred for 4 h in an atmosphere of H2. The reaction was filtered to remove the Pd catalyst and the solvent was evaporated to give ethyl 5-methyl-4-oxo-1H-quinoline-3-carboxylate (145 mg, 22%).

Workup

  1. customwas flushed under a N2
  2. customby evacuating under vacuum
  3. additionAcetic acid (21 mL) was added under an inert atmosphere
  4. customby evacuating under vacuum
  5. filtrationThe reaction was filtered
  6. customto remove the Pd catalyst
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-092afdf2d12145bebd0d3dd315ae1b84
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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