Reacción #1483072

Ecuación de reacción

1-(3-nitrobenzyl)-1H-indole-6-carboxylic acid methyl ester

→

1-(3-aminobenzyl)-1H-indole-6-carboxylic acid methyl ester

Rendimiento 105.3%

Disolventes

MeOH

AcOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Filtraciónthe solids were filtered
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate (150 ml)
3. 3
   Lavadowashed with sat. NaHCO3 (200 ml)
4. 4
   SecadoThe organic layer was dried (MgSO4)
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated

Procedimiento

To a solution of 1-(3-nitrobenzyl)-1H-indole-6-carboxylic acid methyl ester (1.3 g, 4.2 mmol) in MeOH (40 mL) and AcOH (3 ml) was added Zinc dust (1.9 g, 29 mmol). After stirring at room temperature for 3 hr, the solids were filtered and the filtrate was diluted with ethyl acetate (150 ml) and washed with sat. NaHCO3 (200 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect 1.24 g (100% yield) of 1-(3-aminobenzyl)-1H-indole-6-carboxylic acid methyl ester. 1H NMR (300 MHz, DMSO) δ 8.02 (s, 1H), 7.64 (m, 3H), 6.92 (t, 1H, J=7.6 Hz), 6.58 (d, 1H, J=3.0 Hz), 6.40 (d, 1H, J=7.6 Hz), 6.27 (m, 2H), 5.36 (s, 2H), 5.07 (s, 2H), 3.81 (s, 3H).

Fuente