反应 #725876

反应方程式

EtOH

N-toluenesulfonyl-2-(4-(trifluoroacetylamino)benzoyl)pyrrole

KOH

→

2-(4-aminobenzoyl)pyrrole

收率 94.0%

溶剂

EtOAc

反应条件

后处理

1. 1
   温度the mixture was heated
2. 2
   温度at reflux until thin layer chromatography (TLC) analysis
3. 3
   其他the mixture was evaporated to dryness
4. 4
   其他The crude product was purified by column chromatography (SiO2, EtOAc:Hexanes)

实验过程

To a stirred EtOH (4 mL) solution containing N-toluenesulfonyl-2-(4-(trifluoroacetylamino)benzoyl)pyrrole (0.500 g, 1.15 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until thin layer chromatography (TLC) analysis showed complete conversion of the starting material. The resulting solution was cooled to room temperature and diluted with EtOAc (20 mL), and the mixture was evaporated to dryness. The crude product was purified by column chromatography (SiO2, EtOAc:Hexanes) to afford the purified product 2-(4-aminobenzoyl)pyrrole (196 mg, 94% yield). 1H NMR (400 MHz, CD2Cl2, 25° C.) δ4.19 (bs, 2H), 6.33 (m, 1H), 6.72 (d, 2H), 6.88 (m, 1H), 7.10 (m, 1H), 7.82 (d, 2H), 9.90 (bs, 1H); 13C NMR (100 MHz, CD2Cl2, 25° C.) δ110.9, 114.2, 118.0, 124.5, 128.5, 131.8, 131.9, 151.3, 183.5; HRMS (EI): m/z 186.0793 (100) {M}+.

来源