Ethyl furo[3,2-b]pyridine-6-carboxylate → Furo[3,2-b]pyridine-6-carboxylic acid

HRID 1383011Notes

Reaction equation

HRID 1383011 reaction equation
[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12]CC)=[O:11])[CH:8]=2)[CH:3]=[CH:2]1>[OH-].[Na+]>[O:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([OH:12])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

3

Reactant 1

HCID 14372157Ethyl furo[3,2-b]pyridine-6-carboxylate

Product 1

HCID 14372158Furo[3,2-b]pyridine-6-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of ethyl furo[3,2-b]pyridine-6-carboxylate (4.5 g, 23.5 mmol) in 1.25M sodium hydroxide (24 mL) was warmed at 60° C. for one hour to give a clear solution. This solution was cooled, filtered through charcoal and made weakly acidic with conc. hydrogen chloride. The precipitated product was extracted into a large volume of diethyl ether/methanol, dried over anhydrous sodium sulfate, filtered and the solvents removed in vacuo. The residue was triturated with ethanol/diethyl ether and collected to give 3.66 g (95% yield), mp: 238°-239° C.

Workup

  1. customto give a clear solution
  2. temperatureThis solution was cooled
  3. filtrationfiltered through charcoal
  4. extractionThe precipitated product was extracted into a large volume of diethyl ether/methanol
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe solvents removed in vacuo
  8. customThe residue was triturated with ethanol/diethyl ether
  9. customcollected
  10. customto give 3.66 g (95% yield), mp: 238°-239° C.

Sources & evidence

ORD record
ord-671faafe25a14f8796e790c80b89f99e
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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