Methanol → Methyl 5-hydroxypyridine-2-carboxylate

HRID 72941Notes

Reaction equation

HRID 72941 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(=O)(=O)(O)O.[CH3:16]O>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O:10][CH3:16])=[O:9])=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Procedure

To a solution of 5-hydroxypyridine-2-carboxylic acid (1.0 g, 7.2 mmol) in methanol (15 mL) was added sulfuric acid (881 μL, 16.53 mmol) dropwise and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, diluted with DCM (100 mL), washed with sat. aq NaHCO3 solution. The organic layer was separated and dried with sodium sulfate, filtered and concentrated in vacuo to give methyl 5-hydroxypyridine-2-carboxylate, which was used without further purification. ESI-MS m/z calc. 150.1. Found 154.1 (M+1)+; Retention time: 0.33 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with DCM (100 mL)
  3. washwashed with sat. aq NaHCO3 solution
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df417fe02e554b87ba2b14a7053f4e85
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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