HCID 178469639, compound → 7-Oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylic acid

HRID 1947556Notes

Reaction equation

HRID 1947556 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[CH:6][N:5]=[C:4]2[CH:13]=[CH:14][S:15][C:3]=12>[OH-].[Na+]>[O:1]=[C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][NH:5][C:4]2[CH:13]=[CH:14][S:15][C:3]1=2

Participants

3

Reactant 1

HCID 178469639HCID 178469639, compound

Product 1

HCID 110088367-Oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylic acidYield 70%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The ethyl 7-hydroxythieno[3,2-b]pyridine-6-carboxylate 3 (1.0 g, 4.5 mmol) was heated to reflux in 15% NaOH for 30 min. After the reaction was completed it was allowed to cool to room temperature and the solid was removed by filtration, washed with water and ether to give the desired compound as an off-white powder (0.6 g, 70% yield). LC/MS (10-99% CH3CN/0.05% TFA gradient over 5 min): m/z 196.0, m/z 210.0, retention time 0.94 minutes. 1H NMR (DMSO-d6) δ: 15.50 (bs, 1.0 H), 14.0 (s, 1.0 H), 8.80 (s, 1.0 H), 8.30 (d, 1.0 H, J=5.4 Hz), 7.48 (d, 1.0 H, J=5.4 Hz).

Workup

  1. customthe solid was removed by filtration
  2. washwashed with water and ether

Sources & evidence

ORD record
ord-272654d25a1544d996205200112bd0fb
Source dataset
uspto-grants-2013_03
Patent number
US08399479B2

Reaction notes

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