HCID 13730806, compound → HCID 19005819, compound

HRID 1742802Notes

Reaction equation

HRID 1742802 reaction equation
[CH:1]([C:4]1([CH3:26])[C:8](=[O:9])[NH:7][C:6]([C:10]2[C:19]([C:20]([OH:22])=[O:21])=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([N+:23]([O-])=O)[CH:16]=3)[N:11]=2)=[N:5]1)([CH3:3])[CH3:2]>[Pd].CO>[NH2:23][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([C:6]1[NH:7][C:8](=[O:9])[C:4]([CH:1]([CH3:2])[CH3:3])([CH3:26])[N:5]=1)[C:19]([C:20]([OH:22])=[O:21])=[CH:18]2

Participants

4

Reactant 1

HCID 13730806HCID 13730806, compound

Product 1

HCID 19005819HCID 19005819, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-isopropyl-4-methyl-5-oxo-2 -imidazolin-2-yl)-6-nitro-3-quinolinecarboxylic acid (212 mg, 0,594 mmol) and methanol (100 mL), a 50 mg quantity of 10% palladium on carbon is added under argon. The mixture is allowed to shake under a hydrogen atmosphere (4 psi) for thirty minutes at room temperature, The catalyst is removed by filtration through diatomaceous earth and then the filtrate is concentrated in vacuo. The concentrate is partitioned between 100 mL portions of chloroform and water and the layers are separated. The organic layer is washed three times with water, dried over anhydrous sodium sulfate and concentrated in vacuo to give formula III 6-amino-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin2-yl)-3-quinolinecarboxylic acid as a yellow solid (170 mg). The purity of this material is determined by TLC on silica gel with chloroform, methanol and acetic acid (220:30:6) elution.

Workup

  1. customfor thirty minutes
  2. customat room temperature
  3. customThe catalyst is removed by filtration through diatomaceous earth
  4. concentrationthe filtrate is concentrated in vacuo
  5. customThe concentrate is partitioned between 100 mL portions of chloroform and water
  6. customthe layers are separated
  7. washThe organic layer is washed three times with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-04711c416616419d8c30a940ee3668cb
Source dataset
uspto-grants-1994_08
Patent number
US05342771

Reaction notes

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