Реакция #670022

Уравнение реакции

4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

aniline

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

Выход 64.5%

N-Phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide

Выход 64.5%

Растворители

dioxane

Условия реакции

Обработка

1. 1
   Концентрированиеconcentrated in vacuo
2. 2
   ТемператураThe residue was cooled in an ice water bath
3. 3
   workup.ADDITIONaqueous 3.6N hydrochloric acid was added
4. 4
   Другоеthe precipitate collected
5. 5
   Промывкаrinsed with aqueous 3.6N hydrochloric acid
6. 6
   Сушкаwater and dried
7. 7
   ДругоеRecrystallization from ethyl alcohol

Методика

A mixture of 4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid (179 mg, 1 mmol), aniline (0.46 mL, 5 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (959 mg, 5 mmol) in 50% aqueous dioxane (10 mL) was allowed to stir at ambient temperature for 17.5 hours, then concentrated in vacuo. The residue was cooled in an ice water bath, aqueous 3.6N hydrochloric acid was added, and the precipitate collected, rinsed with aqueous 3.6N hydrochloric acid then water and dried. Recrystallization from ethyl alcohol afforded N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamide (Compound 35) (164 mg). mp 225-226° C.

Источник