Reaktion #732502

Reaktionsgleichung

EtOH

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

KOH

→

2-(4-aminobenzoyl)pyrrole

Ausbeute 94.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux until thin layer chromatography (TLC) analysis
3. 3
   Sonstigethe mixture was evaporated to dryness
4. 4
   SonstigeThe crude product was purified by column chromatography (SiO2, EtOAc:Hexanes)

Vorschrift

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.) δ 4.19 (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.) δ 110.9, 114.2, 118.0, 124.5, 128.5, 131.8, 131.9, 151.3, 183.5; HRMS (EI): m/z 186.0793 (100) {M}+.

Quelle