Furo[2,3-b]pyridine-2,5-dicarboxylic acid → Furo[2,3-b]pyridine-5-carboxylic acid

HRID 1383014Notes

Reaction equation

HRID 1383014 reaction equation
[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=[C:4]2[CH:3]=[C:2]1C(O)=O>N1C2C(=CC=CC=2)C=CC=1.C(Cl)(Cl)Cl.C(OCC)C.CO.[Cu]>[O:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]([OH:12])=[O:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

6

Reactant 1

HCID 14372167Furo[2,3-b]pyridine-2,5-dicarboxylic acid

Product 1

HCID 14372168Furo[2,3-b]pyridine-5-carboxylic acidYield 63.4%

Reagents, catalysts & solvents 4

HCID 23978CopperCatalystHCID 6212ChloroformSolventHCID 7047QuinolineSolventHCID 21864698Diethyl ether methanolSolvent

Conditions

Temperature
200 °C

Procedure

A suspension of furo[2,3-b]pyridine-2,5-dicarboxylic acid (5.35 g, 25.9 mmol) in quinoline (40 mL) containing copper dust (2.5 g) was heated under a nitrogen atmosphere at 200° C. for one hour. The cooled mixture was diluted with chloroform and filtered to remove suspended material. The product was extracted into sodium carbonate solution. This solution was carefully acidified with conc. hydrochloric acid and the precipitated product isolated by filtration. This material was dissolved in a large volume of diethyl ether/methanol, dried over anhydrous sodium sulfate and filtered through a pad of charcoal. The solvents were removed in vacuo and the residue triturated with diethyl ether to give pure product (2.68 g, 63% yield), mp: 274°-275° C.

Workup

  1. filtrationfiltered
  2. customto remove
  3. extractionThe product was extracted into sodium carbonate solution
  4. customthe precipitated product isolated by filtration
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered through a pad of charcoal
  7. customThe solvents were removed in vacuo
  8. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-65f1c7ef4d8440dbb9f2c76057f4a082
Source dataset
uspto-grants-1989_02
Patent number
US04808595

Reaction notes

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