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

HRID 1264170Notes

Reaction equation

HRID 1264170 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].[H-].[Na+].C(OCC)=O>O>[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

6

Reactant 4

HCID 6342AcetonitrileHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 99479742-Cyclopropyl-4-(4-fluorophenyl)-3-quinolinecarboxaldehyde

Product 1

HCID 533950303-[2-Cyclopropyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrileYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a flask similar to that employed in Example 1 were placed under argon atmosphere 1.96 g (6.73 mmol) of 2-cyclopropyl-4-(4-fluorophenyl)quinoline-3-carbaldehyde, 10 mL of acetonitrile and 0.434 g (10.9 mmol) of sodium hydride (purity: 60%). The content was stirred at room temperature for 2 hours. The resulting mixture was chilled to 0° C. To the chilled mixture was added 0.85 mL (10.5 mmol) of ethyl formate, and the mixture was stirred for 4 hours at the same temperature. Subsequently, to the mixture was slowly added 10 mL of chilled water. The mixture was then extracted with 30 mL of ethyl acetate which was previously chilled in an ice bath. The organic portion was dried over anhydrous magnesium sulfate, and filtered. The filtrate was analyzed by high performance liquid chromatography (absolute quantitative analysis). It was confirmed that 1.74 g (yield: 82%) of 3-[2-cyclo-propyl-4-(4-fluorophenyl)-3-quinolyl]prop-2-enenitrile was produced.

Workup

  1. customIn a flask similar to that employed in Example 1
  2. temperatureThe resulting mixture was chilled to 0° C
  3. stirringthe mixture was stirred for 4 hours at the same temperature
  4. extractionThe mixture was then extracted with 30 mL of ethyl acetate which
  5. temperaturewas previously chilled in an ice bath
  6. dry with materialThe organic portion was dried over anhydrous magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0dd5a3bdc4394b61a03971c1829c949b
Source dataset
uspto-grants-2003_04
Patent number
US06541636B2

Reaction notes

Loading…