Pyrazole → 4-(1-Pyrazolyl)benzonitrile

HRID 2117613Notes

Reaction equation

HRID 2117613 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH:14]=[CH:13][CH:12]=[N:11]1.[H-].[Na+]>CN(C=O)C.O.CCOC(C)=O>[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[N:11]1

Participants

7

Reactant 3

HCID 1048PyrazoleHCID 145174-FluorobenzonitrileHCID 24758Sodium hydride

Product 1

HCID 120796294-(1-Pyrazolyl)benzonitrileYield 76.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 4-fluorobenzonitrile (1.5 g, 12.35 mmol) and pyrazole (0.843 g, 12.38 mmol) in DMF (10 mL) was added NaH (60% in oil, 0.644 g, 16.09 mmol). The reaction was heated to 145° C. for 20 h. The reaction was cooled to room temperature and was diluted with water and EtOAc The aqueous layer was washed with EtOAc (3×) and the combined organic layers were washed with water (4×). The organic solution was dried (MgSO4, filtered, and concentrated. Medium pressure chromatography (4:1 hexanes:EtOAc) provided 4-pyrazol-1-yl-benzonitrile (1.6 g) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 1H), 7.82 (d, 2H), 7.73 (m, 3H), 6.87 (d, 1H); MS 170 (M+1).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwas washed with EtOAc (3×)
  3. washthe combined organic layers were washed with water (4×)
  4. dry with materialThe organic solution was dried (MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e9c13091e7744932b5330025e0bd7a90
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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