Hydrogen Bromide → HCID 54507242, compound

HRID 1195742Notes

Reaction equation

HRID 1195742 reaction equation
C([O:8][C:9]1[C:10]2[N:11]([C:16]([CH:20]=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH:12]=[C:13]([Cl:15])[CH:14]=1)C1C=CC=CC=1.Br.[OH-].[Na+]>C(O)(=O)C>[Cl:15][C:13]1[CH:14]=[C:9]([OH:8])[C:10]2[N:11]([C:16]([CH:20]=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 21873981HCID 21873981, compound

Product 1

HCID 54507242HCID 54507242, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.5 g 8-benzyloxy-6-chloro-3-formyl-2-methyl-imidazo[1,2-a]pyridine, 2.5 ml acetic acid and 2.5 ml 48% aqueous hydrogen bromide solution is heated under reflux for 2 hours. The mixture is cooled to room temperature, poured over 50 ml icewater, neutralized with 1 N-sodium hydroxide solution and extracted 3×with 20 ml ethyl acetate each time. The combined extracts are dried over sodium sulfate, the solvent is stripped off and the solid residue is recrystallized from dioxane. 0.2 g of the title compound of m.p. 256° C. (decomposition) is obtained.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 2 hours
  3. additionpoured over 50 ml icewater
  4. extractionextracted 3×with 20 ml ethyl acetate each time
  5. dry with materialThe combined extracts are dried over sodium sulfate
  6. customthe solid residue is recrystallized from dioxane

Sources & evidence

ORD record
ord-88935400c29747c4af78920106558dff
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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