Sodium Hydroxide → HCID 22254425, compound

HRID 1839096Notes

Reaction equation

HRID 1839096 reaction equation
[N:1]1([CH2:14][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[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH2:14][CH2:15][O:16][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[CH:21][CH:20]=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 99907901H-Imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 22254425HCID 22254425, compoundYield 78.3%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(1H-Imidazo[4,5-c]quinolin-1-yl)ethanol (1.5 g, 7.0 mmol) was added to a stirring mixture of α-bromo-p-tolunitrile (1.79 g, 9.1 mmol), sodium hydroxide (20 ml, 50%), dichloromethane (20 ml), and benzyltrimethylammonium chloride (0.06 g, 0.3 mmol). The reaction was maintained for 18 hours and then diluted with dichloromethane (20 ml) and water (20 ml). The two phases were separated and the aqueous fraction was extracted with additional dichloromethane. The organic fractions were combined, washed with water, dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol) to provide 1.8 g of 4-{[2-(1H-imidazo[4,5-c]quinolin-1-yl)ethoxy]methyl}benzonitrile.

Workup

  1. temperatureThe reaction was maintained for 18 hours
  2. customThe two phases were separated
  3. extractionthe aqueous fraction was extracted with additional dichloromethane
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography (silica gel, 9/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-4110faba151f45f78d6e0d635843567a
Source dataset
uspto-grants-2004_01
Patent number
US06677348B2

Reaction notes

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