Methanol → HCID 178498304, compound

HRID 1721686Notes

Reaction equation

HRID 1721686 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][N:3]=1.S(=O)(=O)(O)O.[CH3:16]O>>[CH3:16][O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178418479HCID 178418479, compound

Product 1

HCID 178498304HCID 178498304, compound

Procedure

To a suspension of 6-hydroxynicotinic acid (20.0 g, 0.144 mol) in methanol as (350 ml) at room temperature was added concentatrated sulfuric acid (9.98 ml, 0.179 mol) and the mixture was refluxed with vigorous stirring for 16 hours. Much of the organic solvent was removed in vacuo. The remaining residue was neutralized with saturated aqueous NaHCO3, and the product was extracted from the aqueous phase with ethyl acetate. The organic layer was dried over MgSO4 and concentrated in vacuo to give 11.50 g of 6-hydroxynicotinic acid methyl ester as a creamish powder.

Workup

  1. temperaturethe mixture was refluxed
  2. customMuch of the organic solvent was removed in vacuo
  3. extractionthe product was extracted from the aqueous phase with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b75609c3761b4bc997c2f10fcc7454fc
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

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