Water → HCID 22320345, compound

HRID 498042Notes

Reaction equation

HRID 498042 reaction equation
[CH3:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]#[N:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:3]=1.S(=O)(=O)(O)[OH:24].O.[OH-].[Na+]>C(O)(=O)C>[CH3:1][C:2]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]=2[C:15]([NH2:16])=[O:24])=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 223201313-Methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-4-carbonitrile

Product 1

HCID 22320345HCID 22320345, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-4-carbonitrile (0.30 g, 1.1 mmol) and conc. sulfuric acid (1.0 mL) in acetic acid (6.0 mL) was heated under reflux for 31.5 hours. The solution was allowed to cool to room temperature, and poured into iced water. The resulting solution was neutralized with an aqueous sodium hydroxide solution, and extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was recrystallized from methanol/isopropylether to give the title compound (0.14 g, 44% yield).

Workup

  1. temperatureunder reflux for 31.5 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas recrystallized from methanol/isopropylether

Sources & evidence

ORD record
ord-5bb2da33e0c8421fbea0b1062749e860
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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