Ethanol → Ethyl 3-hydroxypicolinate

HRID 1804630Notes

Reaction equation

HRID 1804630 reaction equation
[OH:1][C:2]1[C:3]([C:8]([OH:10])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.[CH2:16](O)[CH3:17]>C1C=CC=CC=1>[OH:1][C:2]1[C:3]([C:8]([O:10][CH2:16][CH3:17])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 134013-Hydroxypicolinic Acid

Product 1

HCID 15080989Ethyl 3-hydroxypicolinateYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 5.0 g (36 mmol) of 3-hydroxylpicolinic acid in 120 mL ethanol and 40 ml benzene was added 2.0 ml of 98% sulfuric acid. The reaction was refluxed for 40 h. After the solvents were evaporated, the residue was dissolved in 100 ml of water, neutralized with saturated sodium bicarbonate solution and extracted with dichloromethane 3 times. The combined organics were dried over magnesium sulfate, filtered and evaporated in vacuo to afford 3.5 g (58% yield) of the title compound as a brown residue that was used without further purification.

Workup

  1. temperatureThe reaction was refluxed for 40 h
  2. customAfter the solvents were evaporated
  3. dissolutionthe residue was dissolved in 100 ml of water
  4. extractionextracted with dichloromethane 3 times
  5. dry with materialThe combined organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a26dffdade5445cd959082efac58063f
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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