Ethanol → HCID 14390205, compound

HRID 2351622Notes

Reaction equation

HRID 2351622 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[N:8]=[C:7]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Br:21])[CH:16]=1)C.C(O)C.[OH-].[Na+]>O>[Br:21][C:17]1[CH:16]=[C:15]([C:7]2[N:6]([CH2:5][C:4]([OH:22])=[O:3])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[N:8]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 14390204HCID 14390204, compound

Product 1

HCID 14390205HCID 14390205, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(3-bromophenyl)-3H-imidazo[4,5-b]pyridine-3-acetic acid ethyl ester (4.8 g, 0.0133 mole), 95% ethanol (50 ml), sodium hydroxide pellets (0.6 g, 0.014 mole), and water (5 ml) was refluxed for 2 hrs. The ethanol was evaporated and water (50 ml) added. Glacial acetic acid was added dropwise until precipitation began (pH neutral). The precipitated solid was collected by filtration and recrystallized from ethanol-tetrahydrofuran, giving 3.9 g (88% yield) of white needles, mp (247°-249° C.

Workup

  1. customThe ethanol was evaporated
  2. additionwater (50 ml) added
  3. additionGlacial acetic acid was added dropwise until precipitation
  4. filtrationThe precipitated solid was collected by filtration
  5. customrecrystallized from ethanol-tetrahydrofuran

Sources & evidence

ORD record
ord-77e3a1486b5f48268112ed6e4f162a37
Source dataset
uspto-grants-1989_10
Patent number
US04873251

Reaction notes

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