Methanol → HCID 45091314, compound

HRID 2370818Notes

Reaction equation

HRID 2370818 reaction equation
[OH:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:3]1.[C:13](=O)([O-])[O-].[K+].[K+].CI.CO>CN(C=O)C>[CH3:13][O:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:3]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21885934Methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 45091314HCID 45091314, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 1-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylate (0.75 g, 4.43 mmol) in 5 mL DMF at 23° C., were added potassium carbonate (1.8 g, 13.3 mmol) and MeI (1.5 g, 11 mmol). The resulting mixture was stirred overnight and then MeOH (6 mL) was added and the resulting mixture was stirred for 2 h. The volatiles were removed under vacuum, and the resulting residue was dissolved in EtOAc (75 mL), washed with water (2×50 mL), brine (50 mL), dried (MgSO4), and concentrated to give methyl 1-methoxy-6-oxo-1,6-dihydropyridine-3-carboxylate as a brown oil.

Workup

  1. stirringthe resulting mixture was stirred for 2 h
  2. customThe volatiles were removed under vacuum
  3. dissolutionthe resulting residue was dissolved in EtOAc (75 mL)
  4. washwashed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ed1218869ea24cc0a2fe9693dbfe2c12
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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