Acetic Anhydride → Furo[3,4-b]pyridine-5,7-dione, 3-bromo-

HRID 1619286

Reaction equation

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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 154810665-Bromopyridine-2,3-dicarboxylic acid

Product 1

HCID 15481067Furo[3,4-b]pyridine-5,7-dione, 3-bromo-Yield 79%

Conditions

Temperature: 80 °C

Procedure

A suspension of 5-bromo-pyridine-2,3-dicarboxylic acid (700 mg, 2.85 mmol) in acetic anhydride (0.88 ml, 9.39 mmol, 3.3 equiv.) was heated at 80° C. for 10 min and then refluxed for 1 h. Acetic anhydride was evaporated off in vacuo. The resulting solid was triturated with hexane to afford 3-bromo-furo[3,4-b]pyridine-5,7-dione (510 mg, 79%) as off white solid.

Workup

temperaturerefluxed for 1 h
customAcetic anhydride was evaporated off in vacuo
customThe resulting solid was triturated with hexane

Sources & evidence

ORD record: ord-5620514277ac489886440e82e1ca835e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772300B2

Linked notes

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