Acetic Anhydride → HCID 14986947, compound

HRID 1292474Notes

Reaction equation

HRID 1292474 reaction equation
[CH3:1][C:2]([CH3:18])([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=[CH:6]1)[CH2:3][OH:4].[C:19](OC(=O)C)(=[O:21])[CH3:20].ClC1C=CC=C(C(OO)=[O:34])C=1>CO>[C:19]([O:4][CH2:3][C:2]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:34])=[CH:9][C:8]=2[N:7]=[CH:6]1)([CH3:18])[CH3:1])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 70297m-Chloroperbenzoic acidHCID 14986944HCID 14986944, compound

Product 1

HCID 14986947HCID 14986947, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 67.8 g (0.281 mole) of beta,beta-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol and 170 mL of acetic anhydride was heated at about 100° C. for three hours. To this solution was added 1700 mL of methanol and the solution was refluxed for about 0.5 hour. The solution was evaporated in vacuo and the residue was basified with a saturated sodium bicarbonate solution. Scratching provided an off-white solid which was separated by filtration, washed with water and dissolved in chloroform. The solution was dried over magnesium sulfate and concentrated to a solid residue. The solid was dissolved in 750 mL of chloroform. To this solution was added 67.3 g (0.312 mole) of meta-chloroperbenzoic acid. The mixture was stirred for three hours, evaporated, then washed with saturated sodium bicarbonate solution. Sodium chloride was added, then the mixture was extracted with chloroform. The organic layer was then dried over magnesium sulfate and concentrated by evaporation in vacuo to provide 1-(2-acetoxy-1,1-dimethylethyl)-1H-imidazo[4,5-c]quinoline-5-oxide.

Workup

  1. temperaturethe solution was refluxed for about 0.5 hour
  2. customThe solution was evaporated in vacuo
  3. customScratching provided an off-white solid which
  4. customwas separated by filtration
  5. washwashed with water
  6. dissolutiondissolved in chloroform
  7. dry with materialThe solution was dried over magnesium sulfate
  8. concentrationconcentrated to a solid residue
  9. dissolutionThe solid was dissolved in 750 mL of chloroform
  10. customevaporated
  11. washwashed with saturated sodium bicarbonate solution
  12. additionSodium chloride was added
  13. extractionthe mixture was extracted with chloroform
  14. dry with materialThe organic layer was then dried over magnesium sulfate
  15. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-8bc8a6631c8d4d25a8ffdbb358a28460
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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