Methanol → 1-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinoline

HRID 1611762Notes

Reaction equation

HRID 1611762 reaction equation
[CH2:1]([CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[CH:7]1)[CH2:4][OH:5])[CH3:2].[OH-].[Na+].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25]Br.CO>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH2:25][O:5][CH2:4][CH:3]([N:6]1[C:18]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:8]=[CH:7]1)[CH2:1][CH3:2]

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 698381-(Bromomethyl)-3-chlorobenzeneHCID 218980232-(1H-imidazo[4,5-c]quinolin-1-yl)-1-butanol

Product 1

HCID 222545191-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinolineYield 92.8%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

2-Ethyl-2-(1H-imidazo[4,5-c]quinolin-1-yl)-1-ethanol (3.0 g, 12.43 mmol), dichloromethane (40 mL), aqueous sodium hydroxide (40 mL of 50%), benzyltrimethylammonium chloride (0.01 g) and 3-chlorobenzyl bromide (2.81 g, 13.67 mmol) were combined and the resulting solution was stirred at ambient temperature overnight. Analysis by TLC (5% methanol in dichloromethane) indicated that the reaction was complete. The reaction was diluted with dichloromethane (100 mL) and water (100 mL). The layers were separated. The aqueous fraction was extracted with dichloromethane. The organic fractions were combined, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel eluting with ethyl acetate) to provide 4.22 g of 1-(1-{[(3-chlorobenzyl)oxy]methyl}propyl)-1H-imidazo[4,5-c]quinoline as a light orange oil.

Workup

  1. customThe layers were separated
  2. extractionThe aqueous fraction was extracted with dichloromethane
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (silica gel eluting with ethyl acetate)

Sources & evidence

ORD record
ord-990733e20c0746ed852be57924e7c9f4
Source dataset
uspto-grants-2006_01
Patent number
US06989389B2

Reaction notes

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