Acetyl chloride → 1,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochloride

HRID 2283728Notes

Reaction equation

HRID 2283728 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[C:13]([C:19]#[N:20])=[N:14][N:15]([CH3:18])[C:16]=1[CH3:17]>C(O)C>[ClH:4].[CH3:17][C:16]1[N:15]([CH3:18])[N:14]=[C:13]2[C:12]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[N:5]=[C:19]2[NH2:20]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 669585954-(2-aminophenyl)-1,5-dimethyl-1H-pyrazole-3-carbonitrile

Product 1

HCID 669587141,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochlorideYield 90.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of acetyl chloride (0.150 g, 1.9 mmol) in ethanol (6.4 mL) was stirred for 15 minutes. 4-(2-Aminophenyl)-1,5-dimethyl-1H-pyrazole-3-carbonitrile (0.270 g, 1.27 mmol) was added, and the reaction was heated at reflux under a nitrogen atmosphere for two hours. A precipitate formed. The mixture was allowed to cool to ambient temperature and then cooled to 0° C. The solid was isolated by filtration, washed with diethyl ether, and dried to provide 285 mg of 1,2-dimethyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochloride as a white solid, mp>250° C.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux under a nitrogen atmosphere for two hours
  3. customA precipitate formed
  4. temperaturecooled to 0° C
  5. customThe solid was isolated by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-4c44da75e11f4364a1dcfddb96e6865e
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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