Water → HCID 10618283, Verbindung

HRID 1974566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1974566
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11](=[O:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)[CH:6]=[C:5]2[CH2:22][CH2:23][CH2:24][C:25]([O:27]CC1C=CC=CC=1)=[O:26].O1CCOCC1.O>CO.[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[C:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:6]1)=[O:21]

Komponenten

6

Edukt 3

HCID 962WaterHCID 312751,4-DioxaneHCID 10552586Benzyl 4-[5-chloro-1-(3-nitrobenzoyl)indol-3-yl]butyrate

Produkt 1

HCID 10618283HCID 10618283, VerbindungAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of benzyl 4-[5-chloro-1-(3-nitrobenzoyl)indol-3-yl]butyrate (1.3 g) in a mixture of methanol (35 ml), 1,4-dioxane (35 ml) and water (5 ml) was added 10% palladium on activated carbon (400 mg), and the mixture was stirred under hydrogen atmosphere (3 atm) at 20° C. for 4 hours. The catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel (40 g) eluting with 2% methanol in chloroform to give 4-[1-(3-aminobenzoyl)-5-chloroindol-3-yl]butyric acid (731 mg) as pale yellow crystals.

Aufarbeitung

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel (40 g)
  4. washeluting with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-3d4c91fe38744679badd3b6cf2b2af15
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05283251

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