Ethyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate → 2H,3H-furo(2,3-b)pyridin-3-one

HRID 1984294Notes

Reaction equation

HRID 1984294 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1C(OCC)=O>Cl>[O:4]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:10]2[C:2](=[O:1])[CH2:3]1

Participants

3

Reactant 1

HCID 54685021Ethyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate

Product 1

HCID 125140462H,3H-furo(2,3-b)pyridin-3-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 3-hydroxyfuro[2,3-b]pyridine-2-carboxylate (3.0 g, 11.23 mmol) was heated under reflux in 10% hydrochloric acid (50 mL) for 3 h. Evaporation of the hydrochloric acid solution gave furo[2,3-b]pyridin-3(2H)-one as the hydrochloride salt (1.73 g). A portion of the furo[2,3-b]pyridin-3(2H)-one hydrochloride was converted to its free base by treated with saturated sodium bicarbonate and extracted with chloroform in preparation for the following step.

Workup

  1. customEvaporation of the hydrochloric acid solution

Sources & evidence

ORD record
ord-57eaf0136b5c4491819f2b2515ff1641
Source dataset
uspto-grants-2009_06
Patent number
US07544693B2

Reaction notes

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