Methyl iodide → N(1)-methyl-2-pyridone-5-carboxylic acid

HRID 2243890Notes

Reaction equation

HRID 2243890 reaction equation
[H-].[Na+].OC1C=CC(C(O)=O)=CN=1.IC.[CH3:15][N:16]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]([O:25]C)=[O:24])=[CH:17]1>CO>[CH3:15][N:16]1[C:21](=[O:22])[CH:20]=[CH:19][C:18]([C:23]([OH:25])=[O:24])=[CH:17]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 597449Methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylateHCID 178418479HCID 178418479, compound

Product 1

HCID 592704N(1)-methyl-2-pyridone-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
62 °C

Procedure

Sodium hydride (2.87 g, 60%, 71.8 mmol) was added slowly to methanol (62.5 mL) with stirring. 6-Hydroxy-nicotinic acid (5 g, 35.9 mmol) was added slowly, and the reaction mixture was heated to 62° C. Iodomethane (8.96 mL, 143.7 mmol) was added and the reaction was stirred overnight. The mixture was then cooled to room temperature and filtered to remove undissolved starting material. The filtrate was concentrated to yield a yellow powder which NMR analysis showed contained the title compound and methyl 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate. This mixture was used in the subsequent reaction.

Workup

  1. stirringthe reaction was stirred overnight
  2. temperatureThe mixture was then cooled to room temperature
  3. filtrationfiltered
  4. customto remove undissolved
  5. concentrationThe filtrate was concentrated
  6. customto yield a yellow powder which NMR analysis

Sources & evidence

ORD record
ord-3e10c2fc38294ba0ab09a8c0f3da2bf8
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

Loading…