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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1623072Generated: October 31, 2026

Selenium Dioxide → (S)-2'-oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-2-carboxylic acid

https://huagongshe.com/reaction/1623072

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSelenium DioxideHCID 24007—
Reactant(S)-2'-Oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-2-carbaldehydeHCID 59594285—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product(S)-2'-oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-2-carboxylic acidHCID 59594306—

Reaction Steps

A mixture of (S)-2-methyl-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (500 mg, 1.66 mmol, described in Intermediate 6) and selenium dioxide (552 mg, 4.97 mmol) in dioxane (30 mL) and H2O (3 mL) was heated at reflux for 18 h. The reaction mixture was allowed to cool, then it was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to give the title compound. MS: m/z=332 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08778957B2
Source datasetuspto-grants-2014_07
ORD IDord-cf2407fb3ef647fb835a3c9960a9fad0
Source noteuspto-grants-2014_07