4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime → 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine

HRID 341836Notes

Reaction equation

HRID 341836 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([C:16](=[N:21]O)[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.C(O)(=O)C.[C].[Pd]>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH2:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 867535164,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime

Product 1

HCID 158384675,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amineYield 85.7%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A portion (4.9 g) of 4,5-dihydro-2-(2-phenylethyl)-6H-imidazo[4,5,1-ij]quinolin-6-one oxime obtained in Step 1 was suspended in methanol (50 mL) and acetic acid (25 mL), followed by stirring at room temperature for 18 hrs under a hydrogen atmosphere in the presence of 10% palladium-carbon (0.5 g). The insoluble matter was separated by filtration with Celite® pad and the filtrate was concentrated; thereafter, the residue was dissolved in water and the pH of the solution was adjusted to about 8 with sodium hydrogencarbonate, followed by extraction with dichloromethane. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate; the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol) to yield the titled compound as pale yellow crystals (4.0 g).

Workup

  1. customThe insoluble matter was separated by filtration with Celite® pad
  2. concentrationthe filtrate was concentrated
  3. dissolutionthereafter, the residue was dissolved in water
  4. extractionfollowed by extraction with dichloromethane
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol)

Sources & evidence

ORD record
ord-40879c93102a41178bcd9e717c77e8a2
Source dataset
uspto-grants-1999_01
Patent number
US05856334

Reaction notes

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