Propargyl bromide → HCID 12114205, compound

HRID 967049Notes

Reaction equation

HRID 967049 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.[OH-].[Na+].[CH2:19](Br)[C:20]#[CH:21]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl>[CH2:21]([O:16][CH2:15][CH2:14][N:1]1[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)[C:20]#[CH:19]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 99907901H-Imidazo[4,5-c]quinoline-1-ethanol

Product 1

HCID 12114205HCID 12114205, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-(1H-Imidazo[4,5-c]quinolin-1-yl)-1-ethanol (28.5 g, 0.133 mol) was added in portions over a period of 1 hour to a mixture of sodium hydroxide (240 mL of 50%), dichloromethane (240 mL), propargyl bromide (39.6 g of 80%, 0.266 mol) and benzyltrimethylammonium chloride (2.46 g, 0.013 mmol). The resulting reaction mixture was allowed to stir at ambient temperature for 16 hours. The layers were separated. The aqueous fraction was extracted with additional dichloromethane. The organic fractions were combined, washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was combined with diethyl ether and the mixture was allowed to stir. An orange solid was isolated by filtration. This material was recrystallized from ethyl acetate to provide 19.8 g of 2-(1H-imidazo[4,5-c]quinolin-1-yl)ethyl (2-propynyl) ether as a yellow crystalline solid, m.p. 124-126° C.

Workup

  1. customThe resulting reaction mixture
  2. customThe layers were separated
  3. extractionThe aqueous fraction was extracted with additional dichloromethane
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. stirringto stir
  8. customAn orange solid was isolated by filtration
  9. customThis material was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-cf4213c505a7423f9bd0168a9ba19231
Source dataset
uspto-grants-2005_10
Patent number
US06953804B2

Reaction notes

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