Reaktion #439088

Reaktionsgleichung

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

Ausbeute 64.5%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated in vacuo
2. 2
   TemperaturThe residue was cooled in an ice water bath
3. 3
   workup.ADDITIONaqueous 3.6 N hydrochloric acid was added
4. 4
   Sonstigethe precipitate collected
5. 5
   Waschenrinsed with aqueous 3.6 N hydrochloric acid
6. 6
   Trocknenwater and dried
7. 7
   SonstigeRecrystallization from ethyl alcohol

Vorschrift

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 3.6 N hydrochloric acid was added, and the precipitate collected, rinsed with aqueous 3.6 N 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.

Quelle