Methyl 2-Chloro-6-methylisonicotinate → Methyl 2-methylisonicotinate

HRID 279611

Reaction equation

HRID 279611 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[C:4]([CH3:12])[N:3]=1>[Pd].CO>[CH3:12][C:4]1[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:7]=[CH:2][N:3]=1

Participants

4

Reactant 1

HCID 2759833Methyl 2-Chloro-6-methylisonicotinate

Product 1

HCID 11542811Methyl 2-methylisonicotinateYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl 2-chloro-6-methyl-pyridine-4-carboxylate (1.8 g, 10 mmol) and 10% palladium-on-charcoal catalyst (200 mg) in methanol (100 ml) was stirred under hydrogen at 5 atmospheres pressure. The catalyst was removed by filtration and the volatiles removed from the filtrate by evaporation. The residue was treated with 10% aqueous sodium hydroxide solution and extracted with ether (3×30 ml). The combined extracts were dried (MgSO4) and the solvent removed by evaporation to give methyl 2-methyl-pyridine-4-carboxylate (800 mg, 53%) as an oil.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe volatiles removed from the filtrate by evaporation
  3. additionThe residue was treated with 10% aqueous sodium hydroxide solution
  4. extractionextracted with ether (3×30 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-92651961e0a34696be7c279b6031b815
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Linked notes

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