Ethanol → HCID 14390205, compound

HRID 1709417Notes

Reaction equation

HRID 1709417 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-aca21ee6bc954061971aaf245668cb8c
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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