2-Methylindole → 6-(2-Methyl-1H-indole-3-carbonyl)-cyclohex-3-enecarboxylic acid

HRID 1013221

Reaktionsgleichung

Reaktionsgleichung von HRID 1013221
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[Al+3].[Cl-].[Cl-].[Cl-].[C:15]1(=[O:25])[O:20][C:18](=[O:19])[C@H:17]2[CH2:21][CH:22]=[CH:23][CH2:24][C@@H:16]12>ClCCCl>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:15]([CH:16]1[CH:17]([C:18]([OH:20])=[O:19])[CH2:21][CH:22]=[CH:23][CH2:24]1)=[O:25])=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

5

Edukt 3

HCID 72242-MethylindoleHCID 98495Tetrahydrophthalic anhydride, cis-HCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 673166696-(2-Methyl-1H-indole-3-carbonyl)-cyclohex-3-enecarboxylic acidAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

2-Methyl indole (50 mmol, 6.55 g) and AlCl3 (50 mmol, 7.3 g) were stirred in 500 mL DCE. cis-1,2,3,6-Tetrahydrophthalic anhydride (50 mmol, 7.6 g) was added and the reaction was heated to 65° C. for 6 h. The reaction was carefully quenched with 10 mL water and stirred overnight. The resulting red solid was filtered, washed with water, and dried to give 15 g of the sub-title compound.

Aufarbeitung

  1. customThe reaction was carefully quenched with 10 mL water
  2. filtrationThe resulting red solid was filtered
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-5de2a19cee944556978bb4253db7bfb1
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981912B2

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