Ethyl 3-hydroxyfuro[2,3-c]pyridine-2-carboxylate → Furo[2,3-C]pyridin-3(2H)-one

HRID 1508198Notes

Reaction equation

HRID 1508198 reaction equation
C(OC([C:6]1[O:14][C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7]=1[OH:15])=O)C>Cl.O>[O:14]1[C:9]2=[CH:10][N:11]=[CH:12][CH:13]=[C:8]2[C:7](=[O:15])[CH2:6]1

Participants

4

Reactant 1

HCID 54723934Ethyl 3-hydroxyfuro[2,3-c]pyridine-2-carboxylate

Product 1

HCID 14199080Furo[2,3-C]pyridin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 3-hydroxyfuro[2,3-c]pyridine-2-carboxylic acid ethyl ester (10 mmol) in 10 mL 25% HCl solution and 5 mL H2O was heated to reflux overnight. After cooling to RT, the reaction mixture was quenched with sat. aq. NaHCO3 solution and extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as brown solid;

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe reaction mixture was quenched with sat. aq. NaHCO3 solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8465752acde40e68505e484cd7c1730
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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