반응 #956135

반응 방정식

(E)-but-2-enal

2,3-Difluoroaniline

NaOH

oleum

Sodium 3-nitrobenzenesulfonate

→

7,8-difluoro-2-methylquinoline

용매

H2O

반응 조건

후처리

1. 1
   workup.ADDITIONwas added until pH 12
2. 2
   추출The mixture was extracted with EtOAc (50 mL×3)
3. 3
   건조The combined organic layers were dried over anhydrous Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The crude product was purified by column chromatography

실험 절차

Sodium 3-nitrobenzenesulfonate (2.7 g, 12 mmol) was dissolved in H2O (3 mL), and oleum (4 mL) was added to the mixture. 2,3-Difluoroaniline was then added to the mixture. The mixture was heated to 105° C. and (E)-but-2-enal (2.34 g, 33.4 mmol) was added dropwise. The mixture was stirred at 120° C. for 1 h. Then the mixture was poured into ice (50 g), and solid NaOH was added until pH 12. The mixture was extracted with EtOAc (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography to afford 7,8-difluoro-2-methylquinoline (1.5 g) as a white solid.

출처