Ethanol → HCID 18983834, compound

HRID 1440464Notes

Reaction equation

HRID 1440464 reaction equation
Br[CH2:2][C:3](=O)[CH3:4].[NH2:6][C:7]1[N:16]=[CH:15][CH:14]=[CH:13][C:8]=1[C:9]([O:11][CH3:12])=[O:10].C(O)C.C(Cl)(Cl)Cl>C(Cl)(Cl)Cl.CO>[CH3:4][C:3]1[N:6]=[C:7]2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][CH:14]=[CH:15][N:16]2[CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6212ChloroformHCID 11715BromoacetoneHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 18983834HCID 18983834, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanolSolvent

Procedure

Bromoacetone (6.5 g, 42.7 m moles) and methyl 2-aminonicotinate (4.8 g, 31.5 m moles) were added to ethanol (50 ml), and the mixture was refluxed under heating for 17 hours. The reaction mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. Saturated aqueous solution of sodium bicarbonate (50 ml) was added to the residue, and the mixture was extracted with chloroform (100 ml×3). The extract was washed with water, dried over MgSO4 and concentrated under reduced pressure. The concentrate was purified by column chromatography on silica gel (eluent:chloroform and then chloroform/methanol=9/1) to give the object compound (4.0 g, yield 85%) as an oily substance.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 17 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionSaturated aqueous solution of sodium bicarbonate (50 ml) was added to the residue
  5. extractionthe mixture was extracted with chloroform (100 ml×3)
  6. washThe extract was washed with water
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by column chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-b799568e675a4e0a9bccb79853c42f4b
Source dataset
uspto-grants-1996_03
Patent number
US05498774

Reaction notes

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