Benzyl Bromide → HCID 18760176, compound

HRID 432683Notes

Reaction equation

HRID 432683 reaction equation
[H-].[Na+].[N:3]1([CH2:16][CH2:17][OH:18])[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1.[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:18][CH2:17][CH2:16][N:3]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:5]=[CH:4]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 99907901H-Imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 18760176HCID 18760176, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, sodium hydride (16.88 g of 60% in mineral oil, 422 mmol) was added in portions to a solution of 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethanol (60.0 g, 281 mmol) in anhydrous N,N-dimethylformamide (600 mL). The alkoxide was allowed to stir for about 1.5 hours. Benzyl bromide (50.2 mL, 422 mmol) was slowly added over a period of about 30 minutes. The reaction mixture was allowed to stir at ambient temperature overnight. Solvent was removed under reduced pressure. The residue was taken up in ethyl acetate, washed several times with water, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide 1-[2-(benzyloxy)ethyl]-1H-imidazo[4,5-c]quinoline as a dark oil.

Workup

  1. stirringto stir at ambient temperature overnight
  2. customSolvent was removed under reduced pressure
  3. washwashed several times with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f35469ef9c8a4e59ad18a8e03631166c
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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