Sodium Acetate → Ethyl 5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 1915219Notes

Reaction equation

HRID 1915219 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10](Br)[CH:11]=[CH:12][C:13]=2[O:17][CH3:18])[NH:8][CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:17][CH3:18])[NH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 102458028-bromo-4-hydroxy-5-methoxy-3-Quinolinecarboxylic acid ethyl ester

Product 1

HCID 9992162Ethyl 5-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylateYield 57%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester (2.3 g, 7.1 mmol), sodium acetate (580 mg, 7.1 mmol) and 10% Pd/C (100 mg) in glacial acetic acid (50 mL) was stirred under H2 (2.5 atm) overnight. The catalyst was removed via filtration, and the reaction mixture was concentrated under reduced pressure. The resulting oil was dissolved in CH2Cl2 (100 mL) and washed with aqueous sodium bicarbonate solution and water. The organic layer was dried, filtered and concentrated. The crude product was purified by column chromatography to afford 5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester as a yellow solid (1 g, 57%).

Workup

  1. customThe catalyst was removed via filtration
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe resulting oil was dissolved in CH2Cl2 (100 mL)
  4. washwashed with aqueous sodium bicarbonate solution and water
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-452f9eb8b7274e6390b2fb730635c8fe
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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