Réaction #302850

Équation de réaction

sodium hydroxide

compound 5

6-bromo-4′-aminoflavone

Sodium cyanoborohydride

paraformaldehyde

→

compound 7

6-bromo-4′-dimethylaminoflavone

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThe obtained mixture was stirred at room temperature for 3 hours
2. 2
   workup.ADDITIONwas added to the reaction solution
3. 3
   Extractionthe obtained mixture was then extracted with 50 ml (25 ml×2) of chloroform
4. 4
   SéchageThe extract was dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

Mode opératoire

Sodium cyanoborohydride (74.5 mg, 1.19 mmol) was slowly added dropwise to an acetic acid solution (10 ml) that contained compound 5 (75 mg, 0.237 mmol) and paraformaldehyde (71.1 mg, 2.37 mmol), while stirring. The obtained mixture was stirred at room temperature for 3 hours. After completion of the reaction, 50 ml of a 1 N sodium hydroxide aqueous solution was added to the reaction solution, and the obtained mixture was then extracted with 50 ml (25 ml×2) of chloroform. 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-bromo-4′-dimethylaminoflavone (compound 7) in the form of a yellow crystal. Yield: 70 mg (yield constant: 85.7%) 1H NMR (300 MHz, CDCl3) δ8.34 (s, 1H), 7.72-7.82 (m, 3H), 7.43 (d, J=9.0 Hz, 1H), 6.70-6.77 (m, 3H), 3.08 (s, 6H). MS m/z 345 (M+).

Source