Phosphorus oxychloride → 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 1789415Notes

Reaction equation

HRID 1789415 reaction equation
[CH2:1]([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)[CH:2]([CH3:4])[CH3:3].P(Cl)(Cl)([Cl:21])=O>>[Cl:21][C:9]1[C:8]2[N:7]=[CH:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 118315721-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

Product 1

HCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

Procedure

A mixture of 9.95 g (0.0412 mole) of 1-isobutyl-1H-imidazo [4,5-c]quinolin-5-oxide (from Example 54) and 100 ml of phosphorus oxychloride was heated at its reflux temperature for 2.5 hours, and was then cooled and poured into ice with stirring. Basification (to pH 9-10) with 50% aqueous sodium hydroxide solution was followed by extraction with dichloromethane. The extracts were dried over sodium chloride and sodium bicarbonate, and were then evaporated to provide a solid residue. A sample of the residue was recrystallized from diethyl ether to provide 4-chloro-1-isobutyl-1H-imidazo [4,5-c]quinoline, m.p. 134°-136° C. Analysis: Calculated for C14H17ClN3 : %C, 64.7; H, 5.4; %N, 16.2; Found: %C, 64.3; %H, 5.3; %N, 16.3.

Workup

  1. temperaturewas heated at its
  2. temperaturereflux temperature for 2.5 hours
  3. temperaturewas then cooled
  4. additionpoured into ice
  5. extractionBasification (to pH 9-10) with 50% aqueous sodium hydroxide solution was followed by extraction with dichloromethane
  6. dry with materialThe extracts were dried over sodium chloride and sodium bicarbonate
  7. customwere then evaporated
  8. customto provide a solid residue
  9. customA sample of the residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-140b435f511a4d6abe847ad623279805
Source dataset
uspto-grants-1987_08
Patent number
US04689338

Reaction notes

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