Acetyl chloride → 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride

HRID 1920255Notes

Reaction equation

HRID 1920255 reaction equation
C([Cl:4])(=O)C.[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:16]([CH3:17])[C:15]([CH3:18])=[N:14][C:13]=1[C:19]#[N:20]>C(O)C>[ClH:4].[CH3:17][N:16]1[C:12]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]=[C:19]([NH2:20])[C:13]=2[N:14]=[C:15]1[CH3:18]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 585001475-(2-aminophenyl)-1,2-dimethyl-1H-imidazole-4-carbonitrile

Product 1

HCID 669859121,2-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, a solution of acetyl chloride (55 mg, 0.70 mmol) in ethanol (10 mL) was stirred for 10 minutes. 5-(2-Aminophenyl)-1,2-dimethyl-1H-imidazole-4-carbonitrile (0.100 g, 0.471 mmol) was added, and the reaction was heated at reflux under nitrogen for one hour and then allowed to cool to room temperature. A solid was present and was isolated by filtration, washed with diethyl ether, air-dried, and further dried under vacuum (6.65 Pa) at room temperature for 30 minutes to provide 89 mg (76%) of 1,2-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine hydrochloride, which was found to have a 1H NMR spectrum consistent with the product.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under nitrogen for one hour
  3. customwas isolated by filtration
  4. washwashed with diethyl ether
  5. customair-dried
  6. customfurther dried under vacuum (6.65 Pa) at room temperature for 30 minutes

Sources & evidence

ORD record
ord-35d869a3745741f4b484e4ebf9f30bef
Source dataset
uspto-grants-2012_05
Patent number
US08168802B2

Reaction notes

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