Reacción #8219

Ecuación de reacción

3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide

dimethyl sulfate

sodium methoxide

2-nitropropane

→

3-(2-methyl-2-nitropropyl)-1H-indole-4-carboxylic acid methyl ester

Disolventes

ethyl acetate

NH4Cl

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe aqueous layer is extracted with ethyl acetate (200 ml)
2. 2
   Secadothe combined organic layers are dried over Na2SO4
3. 3
   Concentraciónconcentrated in vacuo

Procedimiento

A 0° C. solution of 3-dimethylaminomethyl-1H-indole-4-carboxylic acid methyl ester hydroiodide (19 g, 52.7 mmol) in 75 ml of methanol and 75 ml of 2-nitropropane is treated with dimethyl sulfate (10 ml, 105.5 mmol) and solid sodium methoxide (6.3 g, 110.6.mmol) sequentially. The resulting mixture is allowed to warm to ambient temperature, and, after stirring overnight, the reaction mixture is diluted with ethyl acetate (300 ml) and saturated aqueous NH4Cl solution (500 ml). The aqueous layer is extracted with ethyl acetate (200 ml), and the combined organic layers are dried over Na2SO4 and concentrated in vacuo to give 3-(2-methyl-2-nitropropyl)-1H-indole-4-carboxylic acid methyl ester in quantitative yield.

Fuente