반응 #725876

반응 방정식

EtOH

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

KOH

→

2-(4-aminobenzoyl)pyrrole

수율 94.0%

용매

EtOAc

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도at reflux until thin layer chromatography (TLC) analysis
3. 3
   기타the mixture was evaporated to dryness
4. 4
   기타The crude product was purified by column chromatography (SiO2, EtOAc:Hexanes)

실험 절차

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}+.

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