Hydrochloric Acid → 3-Bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine

HRID 613619Notes

Reaction equation

HRID 613619 reaction equation
C([O:4][C:5]1[C:6]2[N:7]([C:11]([Br:15])=[C:12]([CH3:14])[N:13]=2)[CH:8]=[CH:9][CH:10]=1)(=O)C.[OH-].[Na+].Cl>CO>[Br:15][C:11]1[N:7]2[CH:8]=[CH:9][CH:10]=[C:5]([OH:4])[C:6]2=[N:13][C:12]=1[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 183218748-Acetoxy-3-bromo-2-methylimidazo[1,2-a]pyridine

Product 1

HCID 183219553-Bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridineYield 75.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 8 -acetoxy-3-bromo-2-methylimidazo[1,2-a]pyridine (235 mg) in methanol (2.5 ml) was added 1N sodium hydroxide solution (2.0 ml) under ice-cooling, and the mixture was stirred for 30 minutes at the same temperature. The mixture was neutralized with 1N hydrochloric acid, and the resulting precipitates were collected by filtration and washed with water to give 3-bromo-8-hydroxy-2-methylimidazo[1,2-a]pyridine (150 mg) as brown powder.

Workup

  1. temperaturecooling
  2. customthe resulting precipitates
  3. filtrationwere collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-fcb8a08985eb4b4f9663ae54a94945aa
Source dataset
uspto-grants-1999_12
Patent number
US06008229

Reaction notes

Loading…