1,3-Dichloroacetone → 2-(Chloromethyl)-8-methylimidazo[1,2-a]pyridine

HRID 2261314Notes

Reaction equation

HRID 2261314 reaction equation
[Cl:1][CH2:2][C:3]([CH2:5]Cl)=O.[NH2:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1>C(O)C>[Cl:1][CH2:2][C:3]1[N:7]=[C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]2[CH:5]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 153472-Amino-3-methylpyridine

Product 1

HCID 32549992-(Chloromethyl)-8-methylimidazo[1,2-a]pyridineYield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.81 g of 1,3-dichloroacetone and 3.24 g of 2-amino-3-methylpyridine were dissolved in 30 ml of ethanol, and the solution was heated to reflux for 5 hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. To the residue, 50 ml of aqueous saturated sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and then recrystallized from hexane-methyl-t-butyl ether to obtain 1.52 g of 2-(chloromethyl)-8-methylimidazo[1,2-a]pyridine.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 5 hours
  3. concentrationconcentrated under reduced pressure
  4. additionTo the residue, 50 ml of aqueous saturated sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customrecrystallized from hexane-methyl-t-butyl ether

Sources & evidence

ORD record
ord-f936955de09e4115a24e0e28e92e070f
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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