Реакция #725878

Уравнение реакции

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

KOH

→

2-(4-aminomethylbenzoyl)pyrrole

Выход 86.5%

Растворители

EtOH

Условия реакции

Обработка

1. 1
   Температураthe mixture was heated
2. 2
   Температураat reflux until TLC analysis
3. 3
   Другоеconsumption of the starting material
4. 4
   Фильтрацияfiltered
5. 5
   Другоеdried

Методика

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}+.

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