反应 #347037

反应方程式

3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline

3,5-di-tert-butyl-4-hydroxy benzoic acid

diethylphosphoryl cyanide

triethylamine

→

4-(2-chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinoline

收率 24.2%

溶剂

water

N,N-dimethylformamide

DMF

反应条件

后处理

1. 1
   workup.STIRRINGThe mixture was stirred at 0° C. for 30 minutes and at room temperature for one night
2. 2
   萃取extracted with ethyl acetate
3. 3
   浓缩The ethyl acetate layer was concentrated
4. 4
   洗涤after being washed with water
5. 5
   干燥dried (MgSO4)
6. 6
   其他The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (85:15,V/V)
7. 7
   其他crystallized from methanol

实验过程

To a mixture of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (1.02 g), 3,5-di-tert-butyl-4-hydroxy benzoic acid (750 mg), diethylphosphoryl cyanide (DEPC) (587 mg) and N,N-dimethylformamide (100 mg) was dropwise added a solution of triethylamine (0.51 ml) in DMF (2 ml) under stirring at 0° C. The mixture was stirred at 0° C. for 30 minutes and at room temperature for one night. Then, the mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was concentrated after being washed with water and dried (MgSO4). The residue was purified by a silica gel column chromatography with hexane-ethyl acetate (85:15,V/V), and then crystallized from methanol to give 4-(2-chlorophenyl)-3-(3,5-di-tert-butyl-4-hydroxybenzamido)-6,8-dimethylquinoline (373 mg, 24.2%). Recrystallization from methanol gave colorless prisms of mp 127°-129° C.

来源