Chloroacetaldehyde → 6-broMo-8-hydroxy-iMidazo[1,2-a] pyridine hydrochloride

HRID 2197568Notes

Reaction equation

HRID 2197568 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[Cl:10][CH2:11][CH:12]=O>CCO>[ClH:10].[Br:9][C:5]1[CH:6]=[C:7]([OH:8])[C:2]2[N:3]([CH:11]=[CH:12][N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 116940412-Amino-5-bromo-3-hydroxypyridine

Product 1

HCID 670075396-broMo-8-hydroxy-iMidazo[1,2-a] pyridine hydrochlorideYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2-Amino-3-hydroxy-5-bromopyridine (Heterocycles, 41:2799 (1995)) (124 mg, 0.65 mmol) was dissolved in EtOH (3 mL) and added chloroacetaldehyde (0.2 mL, 1.3 mmol, 50% in water) and the resulting solution heated at 60° C. overnight. The solvents were then removed and the solids were crystallized from acetone to give 6-bromoimidazo[1,2-a]pyridin-8-ol hydrochloride (151 mg, 92%).

Workup

  1. customThe solvents were then removed
  2. customthe solids were crystallized from acetone

Sources & evidence

ORD record
ord-01159e8c92894e4da2bab05f2cef3e74
Source dataset
uspto-grants-2012_12
Patent number
US08338604B2

Reaction notes

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