Hydrochloric Acid → 3-Methyl-1-(2-pyridinyl)-6-(trifluoromethyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-one

HRID 498027Notes

Reaction equation

HRID 498027 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[N:5]=[C:4]2[N:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=3)[N:17]=[C:18]([CH3:19])[C:3]=12.Cl.C([OH:29])C>>[CH3:19][C:18]1[C:3]2[C:2](=[O:29])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=3)[NH:5][C:4]=2[N:16]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)[N:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 223202634-Chloro-3-methyl-1-(2-pyridinyl)-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 1354446083-Methyl-1-(2-pyridinyl)-6-(trifluoromethyl)-1,9-dihydro-4H-pyrazolo[3,4-b]quinolin-4-oneYield 76%

Procedure

To a solution of 4-chloro-3-methyl-1-(2-pyridinyl)-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]quinoline (6.50 g, 17.9 mmol) in ethanol (300 mL), 6N hydrochloric acid (10 mL, 60 mmol) was added and the mixture was heated under reflux for 5 hours. The solution was allowed to cool to room temperature, and the resulting crystals were collected by filtration. The crystals were washed with ethanol and air dried, and recrystallized from ethanol to give the title compound (4.69 g, 76% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. filtrationthe resulting crystals were collected by filtration
  4. washThe crystals were washed with ethanol and air
  5. customdried
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-16506ba55972411aa511805a3aceac11
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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