Sodium Hydroxide → HCID 22254425, compound

HRID 433977Notes

Reaction equation

HRID 433977 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.[CH:17]1[C:22]([CH2:23]Br)=[CH:21][CH:20]=[C:19]([C:25]#[N:26])[CH:18]=1.[OH-].[Na+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[N:1]1([CH2:14][CH2:15][O:16][CH2:23][C:22]2[CH:21]=[CH:20][C:19]([C:25]#[N:26])=[CH:18][CH:17]=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 a-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-83c5abe6829d4b5ab60c3408191bdd30
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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