Acetic Anhydride → HCID 178448614, compound

HRID 1292482Notes

Reaction equation

HRID 1292482 reaction equation
[CH3:1][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-])=[CH:9][C:8]=2[N:7]=[CH:6]1)([CH3:4])[CH3:3].C(OC(=O)C)(=[O:21])C>>[CH3:1][C:2]([N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([OH:21])[C:8]=2[N:7]=[CH:6]1)([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 14986963HCID 14986963, compound

Product 1

HCID 178448614HCID 178448614, compound

Conditions

Temperature
20 °C

Procedure

To 50 mL of acetic anhydride was added 11.5 g (0.0477 mole) of 1-(1,1-dimethylethyl)-1H-imidazo-[4,5-c]quinoline-5-oxide (product of Example 13) and the slurry was heated on a steam bath for a few minutes, then allowed to cool to about 20° C. The solid was separated by filtration and washed with an ethanol-hexane mixture. Slurring with dilute ammonium hydroxide, filtration and washing with water provided solid which has recrystallized from an ethanol-dichloromethane mixture to provide colorless (white) crystals of 1-(1,1-dimethylethyl)-1H-imidazo[4,5-c]-quinolin-4-ol, m.p. greater than 300° C. Analysis: Calculated for C14H15N3O: % C, 69.7; % H, 6.3; % N, 17.4; Found: % C, 69.5; % H, 6.3; % N, 17.3.

Workup

  1. temperaturethe slurry was heated on a steam bath for a few minutes
  2. customThe solid was separated by filtration
  3. washwashed with an ethanol-hexane mixture
  4. filtrationSlurring with dilute ammonium hydroxide, filtration
  5. washwashing with water provided solid which
  6. customhas recrystallized from an ethanol-dichloromethane mixture

Sources & evidence

ORD record
ord-1e0e256547cc421aaac721d3b3259e90
Source dataset
uspto-grants-1998_05
Patent number
US05756747

Reaction notes

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