Water → 4-(4-formyl-1H-pyrazol-1-yl)benzonitrile

HRID 1969436Notes

Reaction equation

HRID 1969436 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]([C:12]1[CH:13]=[N:14][NH:15][CH:16]=1)=[O:11].[H-].[Na+].O>CN(C=O)C>[CH:10]([C:12]1[CH:13]=[N:14][N:15]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:16]=1)=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 51306731H-pyrazole-4-carbaldehyde

Product 1

HCID 432594404-(4-formyl-1H-pyrazol-1-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 4-fluorobenzonitrile (2.49 g, 20.6 mmol) and 4-formylpyrazole (1.98 g, 20.6 mmo) in 50 mL of DMF at 0° C. was added 95% sodium hydride (0.54 g, 22.7 mmol) under nitrogen. The mixture was heated to 60° C. for 6 hours and cooled to room temperature. Water was added carefully and the mixture was then extracted with ethyl acetate. The combined extracts were washed with water and brine, and then dried over sodium sulfate, filtered, and concentrated in vacuo to provide crude 4-(4-formyl-1H-pyrazol-1-yl)benzonitrile.

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was then extracted with ethyl acetate
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a83fa2f2c2794fd59dce8524a43e0718
Source dataset
uspto-grants-2013_04
Patent number
US08426598B2

Reaction notes

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