HCID 21022905, compound → HCID 70649687, compound

HRID 869001Notes

Reaction equation

HRID 869001 reaction equation
[CH3:1][C:2]1[N:3]([CH3:15])[C:4]2[C:5]([N:14]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]1>Cl.C(O)C.[Pt](=O)=O>[CH3:1][C:2]1[N:3]([CH3:15])[C:4]2[C:5]([N:14]=1)=[C:6]1[C:11](=[CH:12][CH:13]=2)[NH:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 1

HCID 21022905HCID 21022905, compound

Product 1

HCID 70649687HCID 70649687, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 2,3-dimethyl-3H-imidazo[4,5-f]quinoline (0.40 g, 2.03 mmol) and platinum(IV) oxide (24 mg, 0.11 mmol) in HCl (6 N, 2 mL) and ethanol (10 mL) was stirred at room temperature under H2 for 24 h. Then ethanol was removed under reduced pressure and the residue was dissolved in EtOAc (20 mL) and sat. NaHCO3 (3 mL), filtered through Celite, washed with EtOAc (10 mL×3), and separated. The water layer was then extracted with EtOAc (10 mL×3). The combined organic layers were dried with Na2SO4 and filtered; and the solvent was removed under reduced pressure to give a yellow solid. The residue was used in the next step without further purification (320 mg). MS (ESI): m/z 202 [M+H]+.

Workup

  1. customThen ethanol was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc (20 mL)
  3. filtrationsat. NaHCO3 (3 mL), filtered through Celite
  4. washwashed with EtOAc (10 mL×3)
  5. customseparated
  6. extractionThe water layer was then extracted with EtOAc (10 mL×3)
  7. dry with materialThe combined organic layers were dried with Na2SO4
  8. filtrationfiltered
  9. customand the solvent was removed under reduced pressure
  10. customto give a yellow solid
  11. customThe residue was used in the next step without further purification (320 mg)

Sources & evidence

ORD record
ord-2d360e20d9de4d6cabf6836d4fe16182
Source dataset
uspto-grants-2015_03
Patent number
US08969349B2

Reaction notes

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