Ethanol → HCID 57545311, compound

HRID 598272Notes

Reaction equation

HRID 598272 reaction equation
[N+](C1C=C(C=CC=1)O[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:13]=[C:12]([NH2:21])[C:11]=2[N:10]=[C:9]1[CH2:22][CH2:23][CH3:24])([O-])=O.[H][H].[CH2:30]([OH:32])[CH3:31]>[Pt]>[CH2:11]([NH:10][C:9]1[CH:31]=[C:30]([CH:24]=[CH:23][CH:22]=1)[O:32][C:16]1[CH:17]=[CH:18][C:19]2[C:20]3[N:8]([CH2:20][CH:19]([CH3:14])[CH3:18])[C:9]([CH2:22][CH2:23][CH3:24])=[N:10][C:11]=3[C:12]([NH2:21])=[N:13][C:14]=2[CH:15]=1)[CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 86626155HCID 86626155, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57545311HCID 57545311, compound

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Procedure

1-(2-Methylpropyl)-7-(3-nitrophenoxy-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (0.254 g, 0.606 mmol), prepared as described in Example 37, was stirred in ethanol (10 mL), and 5% platinum on carbon (0.025 g) was added. The reaction was placed under a positive pressure of hydrogen and stirred for one hour. The reaction mixture was filtered through a layer of CELITE filter aid, and the filter cake was washed with methanol. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5). The product was recrystallized from acetonitrile to provide 0.032 g of 7-(3-ethylaminophenoxy)-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine as square, orange crystals, mp 168-174° C.

Workup

  1. filtrationThe reaction mixture was filtered through a layer of CELITE
  2. filtrationfilter aid
  3. washthe filter cake was washed with methanol
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluting with dichloromethane:methanol ranging in ratios from 98:2 to 95:5)
  6. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d9853a1f85ff4f59b5507270efe6d19e
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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