3-Hydroxyanthranilic Acid → 1,3-Benzoxazole-4-carboxylic acid

Reaction equation

[NH2:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](OC)(OC)OC>>[O:11]1[C:10]2=[CH:9][CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]2[N:1]=[CH:12]1

Participants

Reactant 2

HCID 863-Hydroxyanthranilic Acid

HCID 9005Trimethyl orthoformate

Product 1

HCID 183546021,3-Benzoxazole-4-carboxylic acid

Procedure

A solution of 2-amino-3-hydroxy-benzoic acid (13.1 mmol) in trimethyl orthoformate (20.0 mL) is refluxed for 4 h, cooled to RT and concentrated in vacuo to give a crude product which is used without further purification.

Workup

concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-83cf8f095fc84f72acb8d92e7c7a4854
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063099B2

Reaction notes

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