Reaction #1483072

Reaction equation

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

→

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

Yield 105.3%

Solvents

MeOH

AcOH

Conditions

Workup

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

Procedure

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