Water → HCID 178498304, compound

HRID 1884332Notes

Reaction equation

HRID 1884332 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.O.[C:17](=O)(O)[O-].[Na+]>CO>[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 178418479HCID 178418479, compound

Product 1

HCID 178498304HCID 178498304, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6-hydroxynicotinic acid (1.00 g, 7.19 mmol) and concentrated sulfuric acid (0.47 ml) in methanol (80 ml) was refluxed for 10 hours then poured into water and sodium bicarbonate (1.45 g) was added. The solvents were evaporated in vacuo and the residue was purified by flash chromatography on silica gel (eluting with 10%-20% methanol in dichloromethane) to give 6-hydroxynicotinic acid, methyl ester as a colourless solid (996 mg, 90%). The product was dissolved in concentrated aqueous ammonia solution and heated at 60° C. for 10 hours. Evaporation of the solvent in vacuo left a solid which was recrystallized from water to give 371 mg, 61% of the title compound as colourless needles.

Workup

  1. additionwas added
  2. customThe solvents were evaporated in vacuo
  3. customthe residue was purified by flash chromatography on silica gel (eluting with 10%-20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5148dcbd272041718a8a13a95581802b
Source dataset
uspto-grants-2004_07
Patent number
US06764829B2

Reaction notes

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