반응 #302850

반응 방정식

sodium hydroxide

compound 5

6-bromo-4′-aminoflavone

Sodium cyanoborohydride

paraformaldehyde

→

compound 7

6-bromo-4′-dimethylaminoflavone

용매

acetic acid

반응 조건

후처리

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
   추출the obtained mixture was then extracted with 50 ml (25 ml×2) of chloroform
4. 4
   건조The extract was dried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONthe solvent was then distilled away under reduced pressure

실험 절차

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+).

출처