Ammonium Hydroxide → 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline

HRID 255568Notes

Reaction equation

HRID 255568 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N+:15]([O-])=[CH:14][C:13]=2[N:12]=[CH:11]1)[CH:7]([CH3:9])[CH3:8].[OH-].[NH4+]>CN(C)C=O>[Cl:3][C:14]1[C:13]2[N:12]=[CH:11][N:10]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:22]=2[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 118315721-isobutyl-1H-imidazo[4,5-c]quinoline-5-oxide

Product 1

HCID 3839614-chloro-1-isobutyl-1H-imidazo[4,5-c]quinolineYield 89.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 40 ml of cold N,N-dimethylformamide (10°-20° C.) was added slowly 5.9 g (0.0385 mole) of phosphorus oxychloride with swirling, the temperature of the mixture being maintained at 10°-20° C. 1-Isobutyl-1H-imidazo[4,5-c]quinolin-5-oxide (6.2 g; 0.0257 mole) from Step (C) above was added gradually with swirling and cooling. After addition was complete, the solution was allowed to stand at room temperature for about 30 minutes with occasional swirling. The solution was then heated on a steam bath for thirty minutes. After allowing it to cool, the solution was poured onto ice with stirring, and the resulting mixture was brought to pH 8-9 with concentrated ammonium hydroxide. The resulting off-white solid was filtered, washed with water, rinsed with ether, and dried to provide 6.0 g of crude 4-chloro-1-isobutyl-1H-imidazo[4,5-c]quinoline having a m.p. of 135°-138° C.

Workup

  1. temperaturethe temperature of the mixture being maintained at 10°-20° C
  2. temperaturecooling
  3. additionAfter addition
  4. temperatureThe solution was then heated on a steam bath for thirty minutes
  5. temperatureto cool
  6. additionthe solution was poured onto ice
  7. filtrationThe resulting off-white solid was filtered
  8. washwashed with water
  9. washrinsed with ether
  10. customdried

Sources & evidence

ORD record
ord-524934cd5e0d4d0ba9c400a2fc2c3436
Source dataset
uspto-grants-1987_10
Patent number
US04698348

Reaction notes

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