Reaktion #161073

Reaktionsgleichung

8-bromo-5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

sodium acetate

→

5-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester

Ausbeute 57.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed via filtration
2. 2
   Einengenthe reaction mixture was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONThe resulting oil was dissolved in CH2Cl2 (100 mL)
4. 4
   Waschenwashed with aqueous sodium bicarbonate solution and water
5. 5
   SonstigeThe organic layer was dried
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe crude product was purified by column chromatography

Vorschrift

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%).

Quelle