Реакция #1483072

Уравнение реакции

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

→

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

Выход 105.3%

Растворители

MeOH

AcOH

Условия реакции

Обработка

1. 1
   Фильтрацияthe solids were filtered
2. 2
   workup.ADDITIONthe filtrate was diluted with ethyl acetate (150 ml)
3. 3
   Промывкаwashed with sat. NaHCO3 (200 ml)
4. 4
   СушкаThe organic layer was dried (MgSO4)
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated

Методика

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).

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