Imidazole → [5-(1H-Imidazol-1-yl)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetic acid

HRID 745930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 745930
F[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]2.C([O-])([O-])=O.[K+].[K+].[NH:22]1[CH:26]=[CH:25][N:24]=[CH:23]1>N1C=CC=CC=1>[N:22]1([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[CH:6]([CH2:12][C:13]([OH:15])=[O:14])[CH2:5]3)[CH:26]=[CH:25][N:24]=[CH:23]1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 10443021HCID 10443021, Verbindung

Produkt 1

HCID 13656050[5-(1H-Imidazol-1-yl)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetic acidAusbeute 39,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 3.3 g of 5-fluoro-2,3-dihydro-1-oxo-1H-indene-2-acetic acid [prepared by following the procedure of G. Cignarella, M. Loriga, G. A. Pinna, M. A. Pirisi, P. Schaitti, and D. Selva, Il Farmaco, Ed. Sci. 37(2), 133-40 (1981)], 2.2 g of anhydrous K2CO3, 1.65 g of imidazole, and 0.15 g of CuO in 15 ml of pyridine is heated to reflux for 24 hours. The reaction mixture is filtered, the filtrate is diluted with water, and the pH of the solution is adjusted to 5. The solid is filtered, washed with water, and crystallized from ethanol to yield 1.6 g of the product, 2,3-dihydro-5-(1H-imidazol-1-yl)-1-oxo-1H-indene-2 acetic acid, mp 224°-226° dec.

Aufarbeitung

  1. customprepared
  2. temperatureto reflux for 24 hours
  3. filtrationThe reaction mixture is filtered
  4. additionthe filtrate is diluted with water
  5. filtrationThe solid is filtered
  6. washwashed with water
  7. customcrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b284097de44142369a71905206642638
Quelldatensatz
uspto-grants-1986_07
Patentnummer
US04602019

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