Ethanol → HCID 57545311, compound

HRID 2383098Notes

Reaction equation

HRID 2383098 reaction equation
[CH3:1][CH:2]([CH3:31])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][C:12]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=4)=[CH:11][C:10]=3[N:9]=[C:8]([NH2:27])[C:7]=2[N:6]=[C:5]1[CH2:28][CH2:29][CH3:30].[H][H].[CH2:34](O)[CH3:35]>[Pt]>[CH2:34]([NH:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:17][C:12]1[CH:13]=[CH:14][C:15]2[C:16]3[N:4]([CH2:3][CH:2]([CH3:31])[CH3:1])[C:5]([CH2:28][CH2:29][CH3:30])=[N:6][C:7]=3[C:8]([NH2:27])=[N:9][C:10]=2[CH:11]=1)[CH3:35]

Participants

5

Reactant 3

HCID 702EthanolHCID 67050983HCID 67050983, 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-db739f58afc34b56b3a9b11e85786324
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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