Potassium Cyanide → 3-Methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-4-carbonitrile

HRID 498041Notes

Reaction equation

HRID 498041 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[C-:22]#[N:23].[K+].C1OCCOCCOCCOCCOCCOC1.[OH-].[Na+]>O1CCCC1.C(#N)C.O>[CH3:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[C:22]#[N:23])=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1

Participants

8

Reactant 4

HCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 2855718-Crown-6HCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 223201313-Methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline-4-carbonitrileYield 50.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (5.89 g, 20.0 mmol), potassium cyanide (2.04 g, 31.3 mmol) and 18-crown-6 (6.96 g, 26.3 mmol) in tetrahydrofuran (90 mL) and acetonitrile (90 mL) was heated under reflux for 8 hours. The solution was allowed to cool to room temperature, and poured into water. The solution was made weakly basic by the addition of a sodium hydroxide solution, and extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvents were evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (chloroform) to give crude crystals. The crude crystals were recrystallized from ethyl acetate to give the title compound (2.86 g, 50% yield).

Workup

  1. temperatureunder reflux for 8 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvents were evaporated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified by silica gel column chromatography (chloroform)
  8. customto give crude crystals
  9. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-66c24de7972e46e989766a9f03ce020d
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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