Ethanol → HCID 14390205, compound

HRID 621868Notes

Reaction equation

HRID 621868 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-6388da8b42ea492d86a3436013e8d52d
Source dataset
uspto-grants-1989_04
Patent number
US04824951

Reaction notes

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