Hydrochloric Acid → 3-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile

HRID 1264176Notes

Reaction equation

HRID 1264176 reaction equation
[CH:1]1([C:4]2[C:13]([CH:14]=O)=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1.[C:23](#[N:25])[CH3:24].C[O-].[Na+].Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH:1]1([C:4]2[C:13]([CH:14]=[CH:24][C:23]#[N:25])=[C:12]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 99479742-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 533950303-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrileYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a flask similar to that of Example 6 were placed under argon atmosphere 1.74 g (5.98 mmol) of 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde, 0.80 mL (15.2 mmol) of acetonitrile, 8.0 mL of tetrahydrofuran (dielectric constant at 25° C.: 7.58), and 0.41 g (7.55 mmol) of sodium methoxide. The content was reacted at 52° C. for 4.5 hours. The resulting mixture was chilled in an ice bath. To the chilled mixture were slowly added under stirring 30 mL of toluene and 7.0 mL (7.00 mmol) of hydrochloric acid (1 mol/L), successively. The separated organic portion was taken out. After washing with two portions of saturated aqueous sodium chloride solution (10 mL), the organic portion was dried over anhydrous magnesium sulfate. The organic portion was then filtered and analyzed by high performance liquid chromatography (absolute quantitative analysis). It was confirmed that 1.64 g (yield: 88%) of 3-[2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinolyl]prop-2-enenitrile was produced.

Workup

  1. customIn a flask similar to that of Example 6 were placed under argon atmosphere
  2. customThe content was reacted at 52° C. for 4.5 hours
  3. temperatureThe resulting mixture was chilled in an ice bath
  4. additionTo the chilled mixture were slowly added
  5. washAfter washing with two portions of saturated aqueous sodium chloride solution (10 mL)
  6. dry with materialthe organic portion was dried over anhydrous magnesium sulfate
  7. filtrationThe organic portion was then filtered

Sources & evidence

ORD record
ord-47306a2781774bae804c82e663157793
Source dataset
uspto-grants-2003_04
Patent number
US06541636B2

Reaction notes

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