Reaktion #302859

Reaktionsgleichung

Tin(II) chloride

compound 23

6-methoxy-4′-nitroflavone

sodium hydroxide

→

compound 24

6-methoxy-4′-aminoflavone

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe obtained mixture was heated
2. 2
   Temperaturto reflux for 1 hour
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Extraktionthe obtained mixture was then extracted with 50 ml of ethyl acetate (150 ml)
5. 5
   TrocknenThe extract was dried over anhydrous sodium sulfate
6. 6
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

Vorschrift

Tin(II) chloride (3.32 g, 17.5 mmol) was slowly added to an ethanol solution (30 ml) that contained compound 23 (520 mg, 1.75 mmol), while stirring. The obtained mixture was heated to reflux for 1 hour. After completion of the reaction, a 1 N sodium hydroxide aqueous solution (150 ml) was added to the reaction solution, and the obtained mixture was then extracted with 50 ml of ethyl acetate (150 ml). The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure, so as to obtain a product of interest, 6-methoxy-4′-aminoflavone (compound 24) in the form of a yellow crystal. Yield: 360 mg (yield constant: 74.8%) 1H NMR (300 MHz, DMSO-d6) δ7.91 (d, J=8.7 Hz, 2H), 7.69-7.70 (m, 1H), 7.38-7.42 (m, 2H), 6.93 (d, J=9.0 Hz, 2H), 6.82 (s, 1H), 3.86 (s, 2H).

Quelle