Chlorotrimethylsilane → Methyl 6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

HRID 2243894Notes

Reaction equation

HRID 2243894 reaction equation
C[N:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([OH:11])=[O:10])=[CH:4][C:3]1=[O:12].Cl[Si](C)(C)[CH3:15]>CO>[CH3:15][O:11][C:9]([C:5]1[CH:6]=[C:7]([CH3:8])[NH:2][C:3](=[O:12])[CH:4]=1)=[O:10]

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 684320291,2-Dihydro-1,6-dimethyl-2-oxo-4-pyridinecarboxylic acid

Product 1

HCID 14117784Methyl 6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylateYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,6-Dimethyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (1.0 g, 6.5 mmol) was suspended in dry methanol (8 mL) and chlorotrimethylsilane (2.8 g, 26 mmol) was added at room temperature. The reaction was stirred for 36 hours at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in a mixture of dichloromethane/methanol (25 mL) and saturated aqueous sodium bicarbonate (25 mL) was added. A precipitate formed which was filtered off and washed with water and MTBE and air-dried. The filtrate was diluted with methanol/dichloromethane and water and the layers were separated. The aqueous layer was extracted once more with dichloromethane. The combined organic layers were dried (sodium sulfate), filtered and concentrated. Both the previously precipitated material and the concentrated organic layer consisted of product and were combined to afford of the title compound (820 mg, 75%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in a mixture of dichloromethane/methanol (25 mL) and saturated aqueous sodium bicarbonate (25 mL)
  3. additionwas added
  4. customA precipitate formed which
  5. filtrationwas filtered off
  6. washwashed with water and MTBE
  7. customair-dried
  8. additionThe filtrate was diluted with methanol/dichloromethane and water
  9. customthe layers were separated
  10. extractionThe aqueous layer was extracted once more with dichloromethane
  11. dry with materialThe combined organic layers were dried (sodium sulfate)
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-8a7f80fe06ad461c8ff8082b129fb176
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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