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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2262838Generated: November 2, 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/2262838

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 10) 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 numberUS07851464B2
Source datasetuspto-grants-2010_12
ORD IDord-f561c3d5a04d41edb1a0c8a5d7aeb393
Source noteuspto-grants-2010_12