HCID 53988412, compound → HCID 13987622, compound

HRID 256187Notes

Reaction equation

HRID 256187 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=O)[C:4](=[CH:8][C:9]2[CH:10]=[C:11]([N:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH:12]=[CH:13][C:14]=2[N+:15]([O-])=O)[NH:3]1>CN(C=O)C.[Pd]>[O:1]=[C:2]1[NH:6][C:5]2=[N:15][C:14]3[CH:13]=[CH:12][C:11]([N:18]4[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:20][CH2:19]4)=[CH:10][C:9]=3[CH:8]=[C:4]2[NH:3]1

Participants

4

Reactant 1

HCID 53988412HCID 53988412, compound

Product 1

HCID 13987622HCID 13987622, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 4-[3-[(2,4-dioxoimidazolin-5-ylidene)methyl]-4-nitrophenyl]-1-piperazinecarboxylate (4.25 g, 10.9 mmol) in DMF (200 mL) was hydrogenated over 10% Pd/C (0.7 g) at 60 p.s.i. After 17 hours, the mixture was filtered through kieselguhr and the solvent removed in vacuo. Evaporation was repeated with two portions (200 mL each) of methanol. Residual solid was suspended in absolute ethanol (200 mL) and glacial acetic acid (8 mL) and stirred at reflux for one hour. The mixture was concentrated in vacuo, the residue suspended in DMF (200 mL) and warmed to solution on a steam bath. Palladium on carbon (0.5 g) was added and heating continued for two hours. The mixture was filtered through kieselguhr, the filtrate concentrated to a slurry and diluted with methanol. The precipitate was collected and crystallized from DMF to afford ethyl 4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]quinolin-7-yl)-1-piperazinecarboxylate, a yellow solid (0.74 g) of analytical purity, m.p. >300° C.

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. customthe solvent removed in vacuo
  3. customEvaporation
  4. temperatureat reflux for one hour
  5. concentrationThe mixture was concentrated in vacuo
  6. temperaturewarmed to solution on a steam bath
  7. additionPalladium on carbon (0.5 g) was added
  8. temperatureheating
  9. waitcontinued for two hours
  10. filtrationThe mixture was filtered through kieselguhr
  11. concentrationthe filtrate concentrated to a slurry
  12. additiondiluted with methanol
  13. customThe precipitate was collected
  14. customcrystallized from DMF

Sources & evidence

ORD record
ord-08c9ddaf80b24691b05e8acdf160af7c
Source dataset
uspto-grants-1987_10
Patent number
US04701459

Reaction notes

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