Methyl iodide → HCID 15224429, compound

HRID 2119873Notes

Reaction equation

HRID 2119873 reaction equation
[CH3:1][CH:2]([CH3:25])[CH2:3][N:4]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=[C:5]1[CH:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:18].[H-].[Na+].[CH3:28]I>CN(C)C=O.CCOCC>[CH3:28][O:18][CH:17]([C:5]1[N:4]([CH2:3][CH:2]([CH3:25])[CH3:1])[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:6]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15224426HCID 15224426, compound

Product 1

HCID 15224429HCID 15224429, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

1-(2-Methylpropyl)-α-phenyl-1H-imidazo[4,5-c]quinoline-2-methanol (5.0 g; 15 mmol, Example 45) was dissolved in N,N-dimethylformamide (25 mL) then added to a cooled (0-5° C.) suspension of sodium hydride (0.5 g; 16.6 mmol) in N,N-dimethylformamide (100 mL). The reaction mixture was stirred at room temperature for about one hour then combined with methyl iodide (1.4 mL; 22.6 mmol). Stirring was continued until the reaction was complete as indicated by thin layer chromatography. The reaction mixture was diluted with ether then quenched with water. The ether layer was separated, washed twice with water, dried over magnesium sulfate then evaporated under vacuum. The residue was triturated with methylene chloride/hexane to provide 4.5 g of a solid. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. additionthen added to
  2. temperaturea cooled
  3. stirringStirring
  4. customthen quenched with water
  5. customThe ether layer was separated
  6. washwashed twice with water
  7. dry with materialdried over magnesium sulfate
  8. customthen evaporated under vacuum
  9. customThe residue was triturated with methylene chloride/hexane

Sources & evidence

ORD record
ord-b4b8791a8e5b43f1a7a3af3abf52aa55
Source dataset
uspto-grants-2004_02
Patent number
US06686472B2

Reaction notes

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