Selenium Dioxide → (+/-)-3'-Methyl-2',5'-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carboxylic acid

HRID 1623083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623083
[CH3:1][N:2]1[C:6]2([CH2:20][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[CH2:7]2)[N:15]=[C:14]([CH:18]=[O:19])[CH:13]=[CH:12]4)[C:5](=[O:21])[NH:4][C:3]1=[O:22].[Se](=O)=[O:24]>O1CCOCC1.O>[CH3:1][N:2]1[C:6]2([CH2:20][C:9]3[CH:10]=[C:11]4[C:16](=[CH:17][C:8]=3[CH2:7]2)[N:15]=[C:14]([C:18]([OH:24])=[O:19])[CH:13]=[CH:12]4)[C:5](=[O:21])[NH:4][C:3]1=[O:22]

Komponenten

5

Edukt 2

HCID 24007Selenium DioxideHCID 57774216(+/-)-3' Methyl-2',5'-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carbaldehyde2×

Produkt 1

HCID 57774222(+/-)-3'-Methyl-2',5'-dioxo-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of (±)-2,3′-dimethyl-6,8-dihydro-2′H,5′H-spiro[cyclopenta[g]quinoline-7,4′-imidazolidine]-2′,5′-dione (500 mg, 1.78 mmol, described in Intermediate 19) and selenium dioxide (592 mg, 5.33 mmol) in dioxane (30 mL) and H2O (3 mL) are heated at reflux for 18 h. The reaction mixture is allowed to cool, filtered through a pad of Celite, and the filtrate is concentrated in vacuo to give the title compound. MS: m/z=312 (M+1).

Aufarbeitung

  1. temperatureare heated
  2. temperatureat reflux for 18 h
  3. temperatureto cool
  4. filtrationfiltered through a pad of Celite
  5. concentrationthe filtrate is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d9b2ae3d1764da28eae379aec4c4e6d
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778957B2

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