Chloroacetone → 8-(2-Methylbenzylamino)-2-methylimidazo[1,2-a]pyridine

HRID 4296

Reaction equation

HRID 4296 reaction equation
[NH2:1][C:2]1[C:7]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:18][C:19](=O)[CH3:20]>C(O)C>[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][NH:8][C:7]1[C:2]2[N:3]([CH:18]=[C:19]([CH3:20])[N:1]=2)[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6571ChloroacetoneHCID 138258912-Amino-3-(2-methylbenzylamino)pyridine

Product 1

HCID 201523218-(2-Methylbenzylamino)-2-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-amino-3-(2-methylbenzylamino)pyridine (3.25 g) and chloroacetone (1.26 ml) in ethanol (65 ml) was refluxed for 18 hours and then evaporated in vacuo. To the residue was added aqueous sodium bicarbonate solution and the mixture was extracted with methylene chloride. The extract was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The oily residue was purified by column chromatography on silica gel (40 g) with a mixture of methylene chloride and ethyl acetate (10:1) as an eluent to give 8-(2-methylbenzylamino)-2-methylimidazo[1,2-a]pyridine (1.80 g).

Workup

  1. customevaporated in vacuo
  2. additionTo the residue was added aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted with methylene chloride
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe oily residue was purified by column chromatography on silica gel (40 g) with a mixture of methylene chloride and ethyl acetate (10:1) as an eluent

Sources & evidence

ORD record
ord-022e022fa6a34c4ca3ba0dec5c804a5d
Source dataset
uspto-grants-1988_02
Patent number
US04725601

Linked notes

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