Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 747346Notes

Reaction equation

HRID 747346 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.OS(O)(=O)=O.[CH3:16]O>>[CH3:16][O:9][C:8](=[O:10])[C:3]1[C:2]([OH:1])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

Procedure

To a stirred solution of 3-hydroxypicolinic acid (0.7122 g, 5.1 mmol) in CH3OH (32 mL) at room temperature was added concentrated H2SO4 (4 mL). The mixture was heated to reflux for 18 hrs then concentrated. The residue was diluted with saturated aqueous Na2CO3 (45 mL) and extracted with CH2Cl2 (4×30 mL). The combined organic phases were dried (Na2SO4) and concentrated to give 0.73 g 3-hydroxypicolinic acid methyl ester as a white powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 18 hrs
  3. concentrationthen concentrated
  4. additionThe residue was diluted with saturated aqueous Na2CO3 (45 mL)
  5. extractionextracted with CH2Cl2 (4×30 mL)
  6. dry with materialThe combined organic phases were dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36f47013b2174245bc243f8b87d8b0cf
Source dataset
uspto-grants-2008_07
Patent number
US07396840B2

Reaction notes

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