Реакция #339666

Уравнение реакции

methyl 3-cyano-1-ethyl-1H-indole-6-carboxylate

methyl 1H-indole-6-carboxylate

NaOH

→

3-cyano-1-ethyl-1H-indole-6-carboxylic acid

Выход 95.1%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Температураheated
2. 2
   Температураat reflux for 2.5 h
3. 3
   Другоеis removed
4. 4
   workup.ADDITIONthe solution is diluted with H2O
5. 5
   Экстракцияextracted with ether (2×)
6. 6
   Экстракцияextracted with EtOAc (3×)
7. 7
   Промывкаwashed with saturated NaCl
8. 8
   Другоеdried
9. 9
   Концентрированиеconcentrated

Методика

A solution of methyl 3-cyano-1-ethyl-1H-indole-6-carboxylate (1.60 g, 7.02 mmol), prepared by the method described in example 1A from methyl 1H-indole-6-carboxylate, in THF (35 mL) is treated with 1N NaOH (7.7 mL, 7.7 mmol) and heated at reflux for 2.5 h. After cooling to room temperature, most of the THF is removed and the solution is diluted with H2O and extracted with ether (2×). The ether extracts are discarded. The aqueous phase is then acidified with 6N HCl to pH 2 and then extracted with EtOAc (3×). The EtOAc layers are combined, washed with saturated NaCl and then dried and concentrated to afford 1.43 g (95%) of 3-cyano-1-ethyl-1H-indole-6-carboxylic acid as a white solid.

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