반응 #67499

반응 방정식

NaOH

2-difluoromethoxy-6-nitro-benzonitrile

tin(II) chloride

hydrochloric acid

→

2-amino-6-difluoromethoxy-benzonitrile

수율 121.0%

용매

water

isopropanol

반응 조건

후처리

1. 1
   온도the reaction mixture is heated
2. 2
   온도to reflux for 30 minutes
3. 3
   추출The mixture is extracted three times with ethyl acetate
4. 4
   건조The combined organic phases are dried over sodium sulfate
5. 5
   농축concentrated

실험 절차

To a solution of 2-difluoromethoxy-6-nitro-benzonitrile (4.0 g, 14.9 mmol) (Example I3) in isopropanol (100 ml) is added tin(II) chloride (10.2 g, 53.6 mmol). Aqueous hydrochloric acid (concentrated) (14.4 ml) is added slowly and the reaction mixture is heated to reflux for 30 minutes. The reaction mixture is cooled to room temperature, diluted with water and the pH is adjusted to 10 by addition of NaOH (2M). The mixture is extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated to yield 2-amino-6-difluoromethoxy-benzonitrile (3.32 g, 93% yield) in pure form. 1H-NMR (CDCl3, 400 MHz): 7.05 (t, 1H), 6.65 (d, 1H), 6.55 (t, 1H), 6.50 (t, 1H), 4.25 (s, br, 2H) ppm.

출처