Réaction #1483072

Équation de réaction

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

→

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

Rendement 105.3%

Solvants

MeOH

AcOH

Conditions de réaction

Traitement

1. 1
   Filtrationthe solids were filtered
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate (150 ml)
3. 3
   Lavagewashed with sat. NaHCO3 (200 ml)
4. 4
   SéchageThe organic layer was dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Mode opératoire

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).

Source