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

HRID 351906

Reaktionsgleichung

Reaktionsgleichung von HRID 351906
[O:1]=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[NH:6][CH:5]=[C:4]([C:11]([OH:13])=O)[C:3]1=2.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC>O1CCOCC1>[C:15]1([NH:14][C:11]([C:4]2[C:3]3[C:2](=[O:1])[CH2:10][CH2:9][CH2:8][C:7]=3[NH:6][CH:5]=2)=[O:13])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 6115AnilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 153376324-Oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylic acid

Produkt 1

HCID 22714666N-phenyl-4-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxamideAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. temperatureThe residue was cooled in an ice water bath
  3. additionaqueous 3.6 N hydrochloric acid was added
  4. customthe precipitate collected
  5. washrinsed with aqueous 3.6 N hydrochloric acid
  6. dry with materialwater and dried
  7. customRecrystallization from ethyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-7fdfc014653a43b7a097ff0381e3abda
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743817B2

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