Butyl iodide → 4H-Imidazo(4,5-c)quinolin-4-one, 1,5-dihydro-5-butyl-1-methyl-

HRID 981905Notes

Reaction equation

HRID 981905 reaction equation
[OH:1][C:2]1[C:11]2[N:12]=[CH:13][N:14]([CH3:15])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[H-].[Na+].[CH2:18](I)[CH2:19][CH2:20][CH3:21]>CN(C)C=O>[CH2:18]([N:3]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[C:10]2[N:14]([CH3:15])[CH:13]=[N:12][C:11]=2[C:2]1=[O:1])[CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 178481229HCID 178481229, compound

Product 1

HCID 30770174H-Imidazo(4,5-c)quinolin-4-one, 1,5-dihydro-5-butyl-1-methyl-Yield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

3.0 g (0.015 mole) of 4-hydroxy-1-methyl-1H-imidazo[4,5-c]quinoline was suspended in 50 ml of dimethylformamide, and 0.80 g (0.020 mole) of 60% sodium hydride was added with ice cooling, followed by stirring at 50° C. for 30 minutes. Then, the mixture was again ice-cooled and 2.6 ml (0.023 mole) of n-butyl iodide was added dropwise, followed by stirring at 50° C. for 2 hours. The solvent was evaporated under reduced pressure, and water was added to the residues, followed by extraction with chloroform. The extract was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: chloroform/methonal=17/1), followed by recrystallization from isopropanol-isopropyl ether, to afford 2.5 g of Compound 1.

Workup

  1. temperaturecooled
  2. stirringby stirring at 50° C. for 2 hours
  3. customThe solvent was evaporated under reduced pressure, and water
  4. additionwas added to the residues
  5. extractionfollowed by extraction with chloroform
  6. washThe extract was washed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluting solvent: chloroform/methonal=17/1)
  11. customfollowed by recrystallization from isopropanol-isopropyl ether

Sources & evidence

ORD record
ord-2828d7e023974cf6be36855caafb0918
Source dataset
uspto-grants-1991_02
Patent number
US04994468

Reaction notes

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