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

HRID 2064764Notes

Reaction equation

HRID 2064764 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

3

Reactant 2

HCID 863-Hydroxyanthranilic AcidHCID 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. LC-MS: tR=0.66 min; [M+H]+=164.1.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba430ae285494c18bda18b0409b7e5f0
Source dataset
uspto-grants-2012_10
Patent number
US08288435B2

Reaction notes

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