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

HRID 656374Notes

Reaction equation

HRID 656374 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

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 16) 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.

Workup

  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

Sources & evidence

ORD record
ord-14df6a8d2e164b819b72a39a611e4b02
Source dataset
uspto-grants-2011_12
Patent number
US08071770B2

Reaction notes

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