Methanol → HCID 18398665, compound

Reaction equation

[S:1]1[C:9]2[C:4](=[N:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13]O>>[S:1]1[C:9]2[C:4](=[N:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

Reactant 2

HCID 887Methanol

HCID 12210216Thieno[3,2-b]pyridine-5-carboxylic acid

Product 1

HCID 18398665HCID 18398665, compoundYield 70%

Procedure

To a cold solution of HCI (10%) in MeOH (10 mL) was added thieno[3,2-b]pyridine-5-carboxylic acid (1.0 g, 5.6 mmol, and the mixture heated to reflux for 2 hr. After cooling to r.t., half the solvent was removed by evaporation and the remainder was partitioned between EtOAc and H2O. Solid NaHCO3 was added until the system remained basic. Separation, drying and evaporation of the organic layer afforded 0.75 g (70%) of the title compound.

Workup

temperaturethe mixture heated
temperatureto reflux for 2 hr
customhalf the solvent was removed by evaporation
customthe remainder was partitioned between EtOAc and H2O
additionSolid NaHCO3 was added until the system
customSeparation
customdrying
customevaporation of the organic layer

Sources & evidence

ORD record: ord-301a2bc90a0d4924ac59dedc883be5da
Source dataset: uspto-grants-1994_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05374635

Reaction notes

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