Реакция #595393

Уравнение реакции

2-Butanone

4-bromophenylhydrazine hydrochloride

→

indole

Выход 67.0%

5-Bromo-2,3-dimethyl-1H-indole

Выход 67.0%

Растворители

EtOH

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was heated
2. 2
   Температураto reflux for 22 h
3. 3
   Концентрированиеconcentrated in vacuo
4. 4
   Другоеpartitioned between EtOAc and 1N HCl
5. 5
   ПромывкаThe organic layer was washed with H2O and saturated aqueous NaHCO3
6. 6
   Сушкаdried over Na2SO4
7. 7
   Фильтрацияfiltered
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеThe crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

Методика

Following a published procedure (Gundersen, E. G. U.S. Patent App. Publ. US 2005/070592) 2-Butanone (0.11 mL, 1.278 mmol) was added to a solution of 4-bromophenylhydrazine hydrochloride (0.300 g, 1.342 mmol in EtOH (3.8 mL). The mixture was heated to reflux for 22 h, concentrated in vacuo, and partitioned between EtOAc and 1N HCl. The organic layer was washed with H2O and saturated aqueous NaHCO3, dried over Na2SO4, filtered, and concentrated. The crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane) to afford the desired indole as a pink powder (200 mg, 67%).

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