Acetic Anhydride → HCID 14986946, compound

HRID 2248090Notes

Reaction equation

HRID 2248090 reaction equation
[CH3:1][CH:2]([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:18](OC(=O)C)(=[O:20])[CH3:19].ClC1C=CC=C(C(OO)=[O:33])C=1>CO>[C:18]([O:4][CH2:3][CH:2]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:10]([O-:33])=[CH:9][C:8]=2[N:7]=[CH:6]1)[CH3:1])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 70297m-Chloroperbenzoic acidHCID 14700378HCID 14700378, compound

Product 1

HCID 14986946HCID 14986946, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 13.1 g (0.058 mole) of beta-methyl-1H-imidazo[4,5-c]quinoline-1-ethanol and 35 mL of acetic anhydride was heated at about 100° C. for two hours. To this solution was added 350 mL of methanol and the solution was stirred for about 0.5 hour. The solution was evaporated in vacuo and the residue was added to a saturated sodium bicarbonate solution. The mixture was extracted with chloroform, the extracts were dried over magnesium sulfate and concentrated to a volume of about 150 mL. To this solution was added 15 g (0.07 mole) of meta-chloroperbenzoic acid. The mixture was stirred for one hour, then washed with chloroform, saturated sodium bicarbonate solution and water. The organic layer was then dried over magnesium sulfate and concentrated by evaporation in vacuo to provide 1-(2-acetoxy-1-methylethyl)-1H-imidazo[4,5-c]-quinolin5-oxide.

Workup

  1. customThe solution was evaporated in vacuo
  2. additionthe residue was added to a saturated sodium bicarbonate solution
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extracts were dried over magnesium sulfate
  5. concentrationconcentrated to a volume of about 150 mL
  6. stirringThe mixture was stirred for one hour
  7. washwashed with chloroform, saturated sodium bicarbonate solution and water
  8. dry with materialThe organic layer was then dried over magnesium sulfate
  9. concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-11f019718aed44419893fe3b2270cabd
Source dataset
uspto-grants-1991_08
Patent number
US05037986

Reaction notes

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