Methanol → HCID 178498560, compound

HRID 594306Notes

Reaction equation

HRID 594306 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=[O:9])[CH:3]=1.OS(O)(=O)=O.[CH3:16]O>>[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:16])=[O:9])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 178524611HCID 178524611, compound

Product 1

HCID 178498560HCID 178498560, compound

Procedure

A mixture of commercially available 4-hydroxypicolinic acid (3.000 g; 21.56 mmol) and concentrated H2SO4 (0.6 ml) in anh. MeOH (40 ml) was refluxed, under nitrogen, for 22 h. MeOH was removed under reduced pressure, and the residue was basified by addition of a solution of 10% aq. NaHCO3. The mixture was then extracted with DCM (3×), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording methyl 4-hydroxypicolinate as a beige solid. LC-MS (conditions A): tR=0.18 min.; [M+H]+: 154.11 g/mol.

Workup

  1. temperaturewas refluxed, under nitrogen, for 22 h
  2. customMeOH was removed under reduced pressure
  3. additionthe residue was basified by addition of a solution of 10% aq. NaHCO3
  4. extractionThe mixture was then extracted with DCM (3×)
  5. dry with materialthe mixed organic layers were dried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-549c6fe4820b42b8932057d91b3acedb
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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