反应 #169155

反应方程式

3,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole

water

E101

→

[3-(3,5-dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine 3-(3,5-dimethyl-4-isoxazolyl)-4-(methyloxy)aniline

收率 100.0%

溶剂

ethanol

EtOAc

反应条件

后处理

1. 1
   其他having first purged the vessel twice with vacuum/nitrogen cycles
2. 2
   其他No hydrogen uptake for the first 8-10 h, then steady uptake till approximately 20 liters had been consumed
3. 3
   其他The mixture purged with vacuum/nitrogen cycle×3
4. 4
   过滤then was filtered through Celite™ under nitrogen
5. 5
   其他the filtrate evaporated in vacuo

实验过程

3,5-Dimethyl-4-[2-(methyloxy)-5-nitrophenyl]isoxazole (for a preparation see Intermediate 1) (43.9 g, 177 mmol) was dissolved in EtOAc (1 liter) diluted with ethanol (1 liter) and added to Pd/C (8 g, 5% w/w, 50% water, Type E101 NO/W) in a 5 liter hydrogenation flask under vacuum, having first purged the vessel twice with vacuum/nitrogen cycles. The mixture was stirred for 24 h. No hydrogen uptake for the first 8-10 h, then steady uptake till approximately 20 liters had been consumed. The mixture purged with vacuum/nitrogen cycle×3 then was filtered through Celite™ under nitrogen and the filtrate evaporated in vacuo to give [3-(3,5-dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine 3-(3,5-dimethyl-4-isoxazolyl)-4-(methyloxy)aniline (38.6 g, 177 mmol, 100% yield) as a brown crystalline solid. LCMS (formate) Rt 0.50 min, MH+ 219

来源