Chloroacetone → 2-Methylimidazo[1,2-a]pyridine

HRID 1293140

Reaction equation

HRID 1293140 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:9][C:10](=O)[CH3:11]>C(O)C>[CH3:11][C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1

Participants

4

Conditions

Temperature
100 °C

Procedure

A mixture of 2-aminopyridine (9.4 g), chloroacetone (9.5 ml), and ethanol (25 ml) was heated and stirred for 5 hours on an oil bath at 100° C. After that, the reaction solution was concentrated under reduced pressure, and extracted with ethyl acetate-aqueous potassium carbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was subjected to a column chromatography using NH silica gel with 20 to 30% ethyl acetate/hexane to yield the title compound (5.5 g).

Workup

  1. temperaturewas heated
  2. concentrationAfter that, the reaction solution was concentrated under reduced pressure
  3. extractionextracted with ethyl acetate-aqueous potassium carbonate solution
  4. washThe organic layer was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ad361289cd24ef7b6f1af38a0deef44
Source dataset
uspto-grants-2007_07
Patent number
US07238720B2

Linked notes

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