Hydrochloric Acid → furo[3,2-b]pyridin-3(2H)-one hydrochloride

HRID 1984288Notes

Reaction equation

[OH:1][C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[O:4][C:3]=1C(OCC)=O.[ClH:16]>>[ClH:16].[O:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:2](=[O:1])[CH2:3]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 54723935Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate

Product 1

HCID 69068905furo[3,2-b]pyridin-3(2H)-one hydrochloride

Procedure

Ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate (6.90 g, 25.8 mmol) was dissolved in 10% hydrochloric acid (50 mL), and heated under reflux for 3 h. Evaporation of the hydrochloric acid solution gave furo[3,2-b]pyridin-3(2H)-one hydrochloride (9.0 g). A portion of the furo[3,2-b]pyridin-3(2H)-one hydrochloride was converted to its free base by treatment with saturated sodium bicarbonate and extraction with chloroform in preparation for the following step.

Workup

temperatureheated
temperatureunder reflux for 3 h
customEvaporation of the hydrochloric acid solution

Sources & evidence

ORD record: ord-3a9f183f7b5f4dc9b6bdf4c48e1c0ac3
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544693B2

Reaction notes

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