Sulfuric Acid → Methyl 3-Hydroxy-2-pyridinecarboxylate

HRID 595549Notes

Reaction equation

HRID 595549 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.[C:16]([O-])([O-])=O.[Na+].[Na+]>CO>[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:16])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylateYield 82.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3-hydroxypicolinic acid (30 g, 0.22 mol) in CH3OH (300 mL) was stirred at RT and conc. H2SO4 (30 mL) was added dropwise. The resulting mixture was stirred at 80° C. overnight. After the pH was adjusted to 7 with solid Na2CO3, the mixture was filtrated and the precipitate was thoroughly washed with EtOAc several times. The filtrate was concentrated to give crude methyl 3-hydroxypicolinate (27 g, yield: 82.8%). 1H-NMR (CDCl3, 400 MHz) δ 10.57 (s, 1H), 8.22˜8.20 (m, 1H), 7.32˜7.29 (m, 1H), 3.93 (s, 3H). MS (M+H)+: 154.

Workup

  1. filtrationthe mixture was filtrated
  2. washthe precipitate was thoroughly washed with EtOAc several times
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-acf95f0920264121ba810aa540a6d9a2
Source dataset
uspto-grants-2016_01
Patent number
US09242998B2

Reaction notes

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