Réaction #725878

Équation de réaction

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

KOH

→

2-(4-aminomethylbenzoyl)pyrrole

Rendement 86.5%

Solvants

EtOH

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   Températureat reflux until TLC analysis
3. 3
   Autreconsumption of the starting material
4. 4
   Filtrationfiltered
5. 5
   Autredried

Mode opératoire

To a stirred EtOH (10 mL) solution containing N-toluenesulfonyl-2-(4-(trifluoroacetylaminomethyl)benzoyl)pyrrole (1.00 g, 2.20 mmol), was added 40% KOH solution (2 mL) and the mixture was heated at reflux until TLC analysis showed complete consumption of the starting material. The reaction mixture was then cooled to room temperature worked up as in Example 7. The crude product was suspended in H2O, filtered and dried to afford the purified product 2-(4-aminomethylbenzoyl)pyrrole (381 mg, 86%). 1H NMR (500 MHz, CD3OD, 25° C.) δ2.43 (s, 3H), 4.53 (s, 2H), 6.42 (m, 1H), 6.77 (m, 1H), 7.41 (d, 2H), 7.72 (d, 2H), 7.85 (m, 1H), 7.95 (d, 2H), 8.39 (t, 1H); 13C NMR (100 MHz, CD3OD, 25° C.) δ44.6, 109.7, 119.4, 125.6, 126.5, 128.4, 130.4, 136.8, 146.1, 184.6; HRMS (EI): m/z 200.0940 (100) {M}+.

Source