Реакция #88079

Уравнение реакции

3-iodo-4-methyl-5-nitro-benzoic acid methyl ester

→

3-amino-5-iodo-4-methyl-benzoic acid methyl ester

Выход 67.3%

Растворители

THF

methanol

Условия реакции

Обработка

1. 1
   Температураcooled to room temperature
2. 2
   Другоеpartitioned between ethyl acetate and saturated aqueous sodium bicarbonate
3. 3
   ДругоеThe organic layer was separated
4. 4
   Сушкаdried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated under reduced pressure
7. 7
   ДругоеThe residue was purified by column chromatography

Методика

To a solution of 3-iodo-4-methyl-5-nitro-benzoic acid methyl ester (2.0 g, 6.23 mmol) in a mixture of THF (40 mL) and methanol (1 mL) was added SnCl2 dihydrate (4.22 g, 18.69 mmol). The reaction mixture was stirred at 60° C. for six hours, then cooled to room temperature and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to afford 1.22 g (67%) of 3-amino-5-iodo-4-methyl-benzoic acid methyl ester.

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