Methyl iodide → HCID 19704385, compound

HRID 260057Notes

Reaction equation

HRID 260057 reaction equation
[H-].[Na+].[CH3:3][CH:4]([OH:20])[CH2:5][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]=[C:7]1[CH3:19].CI.[CH3:23]CCCCC>O1CCCC1.O>[CH3:23][O:20][CH:4]([CH3:3])[CH2:5][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]=[C:7]1[CH3:19]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 24758Sodium hydrideHCID 19704391HCID 19704391, compound

Product 1

HCID 19704385HCID 19704385, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (1 g of 60% ) was added to a suspension of 5 g (0.021 mole) of α,2-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol in 100 mL of tetrahydrofuran. The resulting mixture was stirred for an hour. Methyl iodide (1.55 mL; 0.025 mole) was added and the reaction mixture was stirred for an hour. The reaction mixture was diluted with water then extracted three times with ethyl acetate. The ethyl acetate extracts were combined, dried over magnesium sulfate then concentrated under vacuum to provide 4.9 g of crude product as a brown oil. The oil was refluxed for one hour with 250 mL of hexane then filtered. The filtrate was cooled and the resulting precipitate was collected and dried to provide 2.4 g of a sticky light yellow powder. A sample was recrystallized from ether to provide 1-(2-methoxypropyl)-2-methyl-1H-imidazo[4,5c]quinoline as a white crystalline solid, m.p. 55°-57° C. The structure was confirmed by nuclear magnetic resonance spectroscopy.

Workup

  1. stirringthe reaction mixture was stirred for an hour
  2. extractionthen extracted three times with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationthen concentrated under vacuum
  5. customto provide 4.9 g of crude product as a brown oil
  6. filtrationthen filtered
  7. temperatureThe filtrate was cooled
  8. customthe resulting precipitate was collected
  9. customdried

Sources & evidence

ORD record
ord-cfdf836cbf4944b2b888253c198af179
Source dataset
uspto-grants-1996_06
Patent number
US05525612

Reaction notes

Loading…