HCID 13936997, compound → HCID 15065145, compound

HRID 979512Notes

Reaction equation

HRID 979512 reaction equation
[Cl:1][C:2]1[C:3]([CH3:19])=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([CH2:8][CH:9]2[NH:13][C:12](=[O:14])[NH:11][C:10]2=O)[CH:7]=1.[H][H]>CN(C)C=O.[Pt]>[Cl:1][C:2]1[C:3]([CH3:19])=[CH:4][C:5]2[N:16]=[C:10]3[NH:11][C:12](=[O:14])[NH:13][C:9]3=[CH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 13936997HCID 13936997, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15065145HCID 15065145, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-[(5-Chloro-4-methyl-2-nitrophenyl)methyl]-2,4-imidazolidinedione (2 g, 7 mmol) in dimethylformamide (30 mL) was hydrogenated over 5% platinum on carbon (0.4 g) at 55 psi until hydrogen uptake ceased. The mixture was heated on a steam bath for two hours, concentrated in vacuo and the residue treated with hot (90° C.) dimethyl sulfoxide. Filtration through infusorial earth and evaporation of the solvent afforded a solid which was washed with ether and suspended in boiling methanol. Filtration gave 1,3-dihydro-7-chloro-6-methyl-2Himidazo[4,5-b]quinolin-2-one (1.40 g, 84%) m.p.>360° C.

Workup

  1. temperatureThe mixture was heated on a steam bath for two hours
  2. concentrationconcentrated in vacuo
  3. additionthe residue treated with hot (90° C.) dimethyl sulfoxide
  4. filtrationFiltration
  5. customthrough infusorial earth and evaporation of the solvent
  6. customafforded a solid which
  7. washwas washed with ether
  8. filtrationFiltration

Sources & evidence

ORD record
ord-f71508191264496ab624bab768c476b2
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

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