Sodium Bicarbonate → HCID 18426828, compound

HRID 1281152Notes

Reaction equation

HRID 1281152 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([CH:9]=[O:10])=[CH:4][C:3]=1[CH3:11].O.[C:13]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:24](=[O:27])(O)[O-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH3:11])=[CH:4][C:5]([CH:9]([O:27][CH3:24])[O:10][CH3:13])=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18426809HCID 18426809, compound

Product 1

HCID 18426828HCID 18426828, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-bromo-2,5-dimethyl-3-pyridinecarboxaldehyde (378 g, 1.77 mmol) in methanol (25 mL) was added p-toluenesulfonic acid hydrate (342 mg, 1.80 mmol), and the mixture was heated at reflux for 1 h. Diluted aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 2-bromo-5-dimethoxymethyl-3,6-dimethylpyridine (423 g, 92%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5013da4bf20f4081a5568b4613bb4517
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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