Methyl iodide → HCID 15224429, compound

HRID 1599742Notes

Reaction equation

HRID 1599742 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-a4ce8be6928a45cd9898e02e839bff8c
Source dataset
uspto-grants-1998_04
Patent number
US05741909

Reaction notes

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