Ethanol → HCID 12399293, compound

HRID 1284095Notes

Reaction equation

HRID 1284095 reaction equation
[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([O:19]CC)=[O:18])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(O)C.[OH-].[Na+]>O>[N:1]1[C:2]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][C:17]([OH:19])=[O:18])=[CH:12][CH:11]=2)=[CH:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12399250HCID 12399250, compound

Product 1

HCID 12399293HCID 12399293, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5.2 g of ethyl 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetate, 20 ml of ethanol, 0.96 g of sodium hydroxide and 5 ml of water is stirred at room temperature for 10 minutes. The ethanol is distilled off under reduced pressure, and the residue is dissolved in water. The solution is adjusted to pH 6 by addition of dilute hydrochloric acid. The crystalline precipitate is filtered off, washed with water, and recrystallized from ethanol to give 2.3 g of 4-(imidazo[1,2-a]pyridin-2-yl)phenylacetic acid as colorless crystals melting at 217°-221°C with decomposition.

Workup

  1. distillationThe ethanol is distilled off under reduced pressure
  2. dissolutionthe residue is dissolved in water
  3. additionThe solution is adjusted to pH 6 by addition of dilute hydrochloric acid
  4. filtrationThe crystalline precipitate is filtered off
  5. washwashed with water
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-be8095519175488cb1597443752ba6bc
Source dataset
uspto-grants-1976_08
Patent number
US03978071

Reaction notes

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