Hydrochloric Acid → Methyl 5-hydroxypyridine-2-carboxylate

HRID 2398517Notes

Reaction equation

HRID 2398517 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([OH:11])=[O:10])=[N:7][CH:8]=1.[CH3:12]O>>[CH3:12][O:10][C:9]([C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][N:7]=1)=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2687405-Hydroxypyridine-2-carboxylic acid

Product 1

HCID 4715126Methyl 5-hydroxypyridine-2-carboxylateYield 70%

Procedure

Gaseous hydrogen chloride was passed through a solution of 5 g of dry 5-hydroxy-2-pyridinecarboxylic acid in 100 ml methanol for 5 hours at 70° C. The mixture was kept for 2 days at room temperature and the solvent removed in vacuo. The residue was taken up in a minimum amount of water and neutralized with ammonium hydroxide. The precipitate was removed by filtration and the ester was separated in 70% yield from the acid by recrystallizing from isopropyl alcohol; m.p. 188°-190°.

Workup

  1. customthe solvent removed in vacuo
  2. customThe precipitate was removed by filtration
  3. customthe ester was separated in 70% yield from the acid
  4. customby recrystallizing from isopropyl alcohol

Sources & evidence

ORD record
ord-9f9bbf76b3a14191bd5ae7b01a597d05
Source dataset
uspto-grants-1977_05
Patent number
US04025333

Reaction notes

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