Chloroacetaldehyde → 8-Methylimidazo(1,2-a)pyridine

HRID 2238633Notes

Reaction equation

HRID 2238633 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])O.[Na+].Cl[CH2:15][CH:16]=O.[OH-].[Na+]>O>[CH3:8][C:7]1[C:2]2[N:3]([CH:15]=[CH:16][N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 33ChloroacetaldehydeHCID 14798Sodium HydroxideHCID 153472-Amino-3-methylpyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 3279578-Methylimidazo(1,2-a)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

18.27 g of 2-amino-3-picoline was dissolved in 150 mL of water, 14.2 g of sodium hydrogen carbonate and 33.2 g of chloroacetaldehyde (40% aqueous solution) were added thereto, and then stirred at room temperature for 4 hours. The solution was adjusted to pH 10 with a 3N aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The insolubles were separated by filtration, and then the filtrate was concentrated to obtain 8-methylimidazo[1,2-a]pyridine [3-1] as a brown oily product.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insolubles were separated by filtration
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ae41e64a464e431ca695cb1c1d1fd9d9
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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