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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2105095Generated: October 26, 2026

Acetic Anhydride → HCID 178423899, compound

https://huagongshe.com/reaction/2105095

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
ReactantSquaric acidHCID 17913—
Reactant1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodideHCID 17902140—
Reactant1-(5-Carboxypentyl)-2,3,3-trimethyl-3H-indol-1-ium iodideHCID 68533817—
SolventAcetic AcidHCID 176—
SolventPyridineHCID 1049—
ProductHCID 178423899HCID 178423899—

Reaction Steps

To 1-(3,5-dinitrobenzyl)-2,3,3-trimethyl-3H-indolium iodide (467 mg) was added 3,4-dihydroxy-3-cyclobuten-1,2-dione (110 mg), 1-(5-carboxypentyl)-2,3,3-trimethyl-3H-indolium iodide (354 mg), pyridine (4.5 ml), acetic acid (4.5 ml) and acetic anhydride (1 ml). The mixture was heated to reflux for 3 hours and the solvent then stripped using rotary evaporation. This crude material was subjected to silica flash column chromatography (eluted with MeOH/DCM). Fractions containing product were combined and stripped of solvent. The resulting material was further purified by reverse phase HPLC (CH3CN/H2O/TFA).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07579140B2
Source datasetuspto-grants-2009_08
ORD IDord-fb931656e7474c99a00cb47b820d5fb4
Source noteuspto-grants-2009_08