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

HRID 2404843Notes

Reaction equation

HRID 2404843 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-a0f400efacea4697ac9068408896b6db
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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