4-Fluorobenzonitrile → 22179-78-8

HRID 1619426Notes

Reaction equation

HRID 1619426 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH2:10][OH:11].Cl.C([O-])(O)=O.[Na+]>O>[F:1][C:2]1[CH:9]=[CH:8][C:5](/[C:6](=[N:10]\[OH:11])/[NH2:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 145174-FluorobenzonitrileHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 596080222179-78-8Yield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of 4-fluorobenzonitrile (1.21 g, 10 mmol) and NH2OH.HCl (0.83 g, 12 mmol) in H2O (5 mL) was added NaHCO3 in portions. The reaction mixture was stirred at room temperature overnight. The mixture was then diluted with H2O (50 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration, the filtrate was concentrated under reduced pressure to give the desired product (1.2 g). MS (ESI): 155 (MH+).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63172fccd1114e67b558f5fc7582dc48
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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