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

HRID 401225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401225
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-cd1ea30864344e22bd66f99e42c5d43c
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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