Reacción #339666

Ecuación de reacción

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

methyl 1H-indole-6-carboxylate

NaOH

→

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

Rendimiento 95.1%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux for 2.5 h
3. 3
   Otrois removed
4. 4
   workup.ADDITIONthe solution is diluted with H2O
5. 5
   Extracciónextracted with ether (2×)
6. 6
   Extracciónextracted with EtOAc (3×)
7. 7
   Lavadowashed with saturated NaCl
8. 8
   Otrodried
9. 9
   Concentraciónconcentrated

Procedimiento

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.

Fuente