Reacción #2439945

Ecuación de reacción

HCl

N-[3-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

ethyl formate

sodium ethoxide

→

N-[3-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide

Rendimiento 84.0%

Disolventes

ethanol

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroproducing a black oil
2. 2
   TemperaturaSubsequently, the reaction mixture was cooled to room temperature
3. 3
   FiltraciónThe suspension was filtered

Procedimiento

N-[3-(2-Oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (0.452 g, 1.54 mmol) and ethyl formate (0.370 mL, 4.60 mmol) were dissolved in anhydrous ethanol (6.50 mL). The resulting solution was treated in dropwise fashion with a 21 wt % solution of sodium ethoxide in ethanol (2.90 mL, 7.69 mmol). This reaction mixture was heated at 78° C. for 1 h, producing a black oil. Subsequently, the reaction mixture was cooled to room temperature, and then the reaction pH was adjusted to pH 1 with dropwise addition of 1M HCl(aq) causing the formation of a pale orange precipitate. The suspension was filtered yielding pure N-[3-(3-Hydroxymethylene-2-oxo-2,3-dihydro-1H-indole-5-carbonyl)-phenyl]-acetamide (0.415 g, 1.29 mmol, 84%).

Fuente