Methanol → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 983630Notes

Reaction equation

HRID 983630 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 (0.7122g, 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-f04da23a8057448db58f13af88aab57c
Source dataset
uspto-grants-2005_03
Patent number
US06864265B2

Reaction notes

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