تفاعل #595393

معادلة التفاعل

2-Butanone

4-bromophenylhydrazine hydrochloride

→

indole

المردود 67.0%

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

المردود 67.0%

المذيبات

EtOH

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture was heated
2. 2
   درجة الحرارةto reflux for 22 h
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىpartitioned between EtOAc and 1N HCl
5. 5
   غسيلThe organic layer was washed with H2O and saturated aqueous NaHCO3
6. 6
   تجفيفdried over Na2SO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated
9. 9
   أخرىThe crude residue was purified by chromatography (SiO2, 0-20% EtOAc/Hexane)

الإجراء التجريبي

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%).

المصدر