Methanol → HCID 178498115, compound

HRID 384100Notes

Reaction equation

HRID 384100 reaction equation
[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:16]O>O>[OH:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178418543HCID 178418543, compound

Product 1

HCID 178498115HCID 178498115, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-hydroxynicotinic acid (3.0 g) in methanol 15 ml, 1 ml of concentrated sulfuric acid was added, and the reaction solution was heated to reflux for 2 hours. The reaction solution was cooled, then the solvent was distilled off under reduced pressure, and the residue obtained was diluted with water and extracted with chloroform. The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to afford the title compound as a pale pink solid.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction solution was cooled
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue obtained
  6. extractionextracted with chloroform
  7. washThe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e58895fc25984385b6357a0fd5e599ec
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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