4-Hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester → 4-hydroxy-3-phenyl-7H-thieno[2,3-b]pyridin-6-one

HRID 215984Notes

Reaction equation

C(OC([C:6]1[C:11](=[O:12])[NH:10][C:9]2[S:13][CH:14]=[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:8]=2[C:7]=1[OH:22])=O)C>[OH-].[Na+]>[OH:22][C:7]1[C:8]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:14][S:13][C:9]=2[NH:10][C:11](=[O:12])[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-Hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester (1.5 g, 4.76 mmol) was refluxed in 2M sodium hydroxide (50 ml) for 5 hr, filtered while still hot, then cooled to 0° C. and acidified to pH 1 by addition of conc. HCl. The resultant white precipitate was filtered and dried to give 4-hydroxy-3-phenyl-7H-thieno[2,3-b]pyridin-6-one as a white solid. Yield=1.05 g (90.7%).

Workup

filtrationfiltered while still hot,
additionacidified to pH 1 by addition of conc. HCl
filtrationThe resultant white precipitate was filtered
customdried

Sources & evidence

ORD record: ord-ffe4c2e9803d4e178f2a7d1e62007a43
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193215B2

Reaction notes

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