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

HRID 745930Notes

Reaction equation

HRID 745930 reaction equation
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

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 10443021HCID 10443021, compound

Product 1

HCID 13656050[5-(1H-Imidazol-1-yl)-1-oxo-2,3-dihydro-1H-inden-2-yl]acetic acidYield 39.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b284097de44142369a71905206642638
Source dataset
uspto-grants-1986_07
Patent number
US04602019

Reaction notes

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