Bromoacetone → 5-Chloro-2-methylimidazo[1,2-a]pyridine hydrobromide

HRID 357018

Reaction equation

HRID 357018 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[Br:9][CH2:10][C:11](=O)[CH3:12]>C(O)C>[BrH:9].[Cl:8][C:4]1[N:3]2[CH:10]=[C:11]([CH3:12])[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 189367145-Chloro-2-methylimidazo[1,2-a]pyridine hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 19.28 g (150 mmol) of 2-amino-6-chloropyridine in 150 ml of ethanol, 25 g (180 mmol) of bromoacetone was added at room temperature, followed by refluxing for 64 hours. After the reaction mixture was cooled, the solvent was distilled off. The residue was purified by recrystallization (solvent: ethanol-ethyl acetate) to yield 20.22 g (54.5%, light brown crystal) of the desired product.

Workup

  1. temperatureby refluxing for 64 hours
  2. temperatureAfter the reaction mixture was cooled
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by recrystallization (solvent: ethanol-ethyl acetate)

Sources & evidence

ORD record
ord-4df35b6cb8814ed7a93fd8fdc541f9cf
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Linked notes

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