Bromoacetone → HCID 22387856, compound

HRID 1072797Notes

Reaction equation

HRID 1072797 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.Br[CH2:13][C:14](=O)[CH3:15]>CC(C)=O>[CH3:15][C:14]1[CH:1]=[C:2]2[N:7]([CH:13]=1)[CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=[CH:3]2

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 22387856HCID 22387856, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 6-methyl-3-pyridinecarboxylate (9.83 g) and bromoacetone (11.8 g) were mixed in acetone (98 ml) and the mixture was refluxed under heating for 20 hr. The solvent was evaporated under reduced pressure and the residue was dissolved in methanol (98 ml). Sodium hydrogencarbonate (16.4 g) was added and the mixture was refluxed under heating for 24 hr. The reaction mixture was concentrated under reduced pressure, water was added and the precipitate was collected by filtration. This was recrystallized from hexane-ethyl acetate to give the objective compound (5.94 g) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 20 hr
  3. customThe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in methanol (98 ml)
  5. additionSodium hydrogencarbonate (16.4 g) was added
  6. temperaturethe mixture was refluxed
  7. temperatureunder heating for 24 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure, water
  9. additionwas added
  10. filtrationthe precipitate was collected by filtration
  11. customThis was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-9230d5b2b5bf45949a7c85672da16ee7
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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