Chloroacetone → HCID 15096960, compound

HRID 846719Notes

Reaction equation

HRID 846719 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1.Cl[CH2:13][C:14](=O)[CH3:15].[OH-].[Na+]>CO>[CH3:15][C:14]1[N:1]=[C:2]2[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]2[CH:13]=1

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 14798Sodium HydroxideHCID 236984Methyl 2-aminopyridine-4-carboxylate

Product 1

HCID 15096960HCID 15096960, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 15 parts of methyl 2-amino-4-pyridinecarboxylate, 13.75 parts of 1-chloro-2-propanone and 160 parts of absolute methanol was stirred and refluxed for 18 hours. The reaction mixture was treated with a sodium hydroxide solution 1N in methanol. The solvent was evaporated in vacuo and the residue was dissolved in trichloromethane. The solution was filtered and the filtrate was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 4-methyl-2-pentanone. The product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 9.7 parts of methyl 2-methylimidazo[1,2-a]pyridine-7-carboxylate; mp. 149.1° C. (intermediate 12).

Workup

  1. temperaturerefluxed for 18 hours
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in trichloromethane
  4. filtrationThe solution was filtered
  5. customthe filtrate was evaporated
  6. customThe residue was purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  8. customThe pure fractions were collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from 4-methyl-2-pentanone
  11. filtrationThe product was filtered off
  12. washwashed with 2,2'-oxybispropane
  13. customdried

Sources & evidence

ORD record
ord-dac46fe4a84e4db1a21439711a930674
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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