Sodium Hydroxide → 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile

HRID 967086Notes

Reaction equation

HRID 967086 reaction equation
[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][OH:16])[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1.Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH:14]([CH2:17][CH3:18])[CH2:15][O:16][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[C:13]2[C:12]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]=[CH:5][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 869964-(Bromomethyl)benzonitrileHCID 218980232-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol

Product 1

HCID 222545174-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrileYield 60.2%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol (3.0 g, 12.4 mmol) was added to a stirring mixture of α-bromo-p-tolunitrile (3.0 g, 15.3 mmol), sodium hydroxide (40 ml, 50%), dichloromethane (40 ml), and benzyltrimethylammonium chloride (0.02 g, 0.11 mmol). The reaction was maintained for 72 hours and then diluted with dichloromethane (100 ml) and water (100 ml). The phases were separated and the aqueous phase was extracted with additional dichloromethane (100 ml). The organic fractions were combined, washed with water, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf 0.48) to provide 2.66 g of 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)butoxy]methyl}benzonitrile.

Workup

  1. temperatureThe reaction was maintained for 72 hours
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with additional dichloromethane (100 ml)
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol, Rf 0.48)

Sources & evidence

ORD record
ord-8cf5779e5baf49d998a63e034232cb35
Source dataset
uspto-grants-2005_10
Patent number
US06953804B2

Reaction notes

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