Dichloromethane → HCID 178419901, compound

HRID 432681Notes

Reaction equation

HRID 432681 reaction equation
C(Br)C#C.ClCCl.[OH-].[Na+].[N:10]1(CCO)[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[CH:11]1>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[NH:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=[CH:11]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7842Propargyl bromide2×HCID 14798Sodium HydroxideHCID 99907901H-Imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 178419901HCID 178419901, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

Benzyltrimethylammonium chloride (0.436 g) and propargyl bromide (6.07 mL of 80%) were added with stirring to a mixture of dichloromethane (185 mL) and aqueous sodium hydroxide (60 mL of 50%). 2-(1H-Imidazo[4,5-c]quinolin-1-yl)ethanol (10.0 g, 46.9 mmol) was added to the resulting solution. The reaction mixture was stirred at ambient temperature for 21 hours at which time analysis by HPLC showed that starting material remained. An additional equivalent of propargyl bromide was added and the reaction mixture was stirred for an additional 46 hours. Water was added to the reaction mixture and the layers were separated. The aqueous fraction was extracted with dichloromethane. The organic fractions were combined, washed with water and with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide a dark brown solid. This material was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane) to provide 7.0 g of 1-[2-propynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline as a brownish solid.

Workup

  1. stirringthe reaction mixture was stirred for an additional 46 hours
  2. customthe layers were separated
  3. extractionThe aqueous fraction was extracted with dichloromethane
  4. washwashed with water and with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide a dark brown solid
  8. customThis material was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-0f1d7af693194972bd4569266f365d1b
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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