Ethanol → HCID 14390205, compound

HRID 2072944Notes

Reaction equation

HRID 2072944 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-7579e250f4984f3da7a985998734b5dc
Source dataset
uspto-grants-1990_04
Patent number
US04914109

Reaction notes

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