Reaction #302859

Reaction equation

Tin(II) chloride

compound 23

6-methoxy-4′-nitroflavone

sodium hydroxide

→

compound 24

6-methoxy-4′-aminoflavone

Solvents

ethanol

Conditions

Workup

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

Procedure

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).

Source