Ammonia → 1-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amine

HRID 1108632Notes

Reaction equation

HRID 1108632 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9](Cl)[C:8]=2[N:7]=[CH:6]1.[NH3:19]>CO>[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]([NH2:19])[C:8]=2[N:7]=[CH:6]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 177767961-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline

Product 1

HCID 187839731-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14 mg (0.0536 mmol) of 1-(3-aminopropyl)-4-chloro-1H-imidazo[4,5-c]quinoline, 5 ml of methanol and 3 ml of liquid ammonia were stirred in an autoclave overnight at 150° C. under heating. The reaction mixture was concentrated under reduced pressure and 0.3 ml of a 1N sodium hydroxide solution was added to the residue. The precipitate thus formed was collected by filtration to obtain 8 mg (0.0331 ml) of 1-(3-aminopropyl)-1H-imidazo[4,5-c]quinoline-4-amine shown below. ##STR38## The physicochemical data of this compound was in agreement with the compound of Example 5.

Workup

  1. temperatureunder heating
  2. concentrationThe reaction mixture was concentrated under reduced pressure and 0.3 ml of a 1N sodium hydroxide solution
  3. additionwas added to the residue
  4. customThe precipitate thus formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-402ea26c54de4db38548a53845d6f89d
Source dataset
uspto-grants-2000_05
Patent number
US06069149

Reaction notes

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