反応 #1483072

反応方程式

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

→

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

収率 105.3%

溶媒

MeOH

AcOH

反応条件

後処理

1. 1
   ろ過the solids were filtered
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate (150 ml)
3. 3
   洗浄washed with sat. NaHCO3 (200 ml)
4. 4
   乾燥The organic layer was dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated

実験手順

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).

出典