Acetic Acid → 4-Amino-2-fluorobenzonitrile

HRID 245026Notes

Reaction equation

HRID 245026 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1)([O-])=O.C(O)(=O)C>[Fe].C(OCC)(=O)C>[NH2:1][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[C:6]([F:12])[CH:5]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 27834134-Amino-2-fluorobenzonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitro-2-fluorobenzonitrile (1.83 g, 5 mmol) and iron (1.68 g, 6 mmol) M a mixture of acetic acid (40 ml) and ethyl acetate (40 ml) was refluxed for 2 hours. The solid was filtered off and the filtrate was washed with water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, concentrated and chromatographed (dichloromethane:acetone, 95:5) to yield 4-amino-2-fluorobenzonitrile (54a) (0.653 g, 4.8 mmol, 96%).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe solid was filtered off
  3. washthe filtrate was washed with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customchromatographed (dichloromethane:acetone, 95:5)

Sources & evidence

ORD record
ord-4cef3d7fcc1f46f2803f956e37d57f1f
Source dataset
uspto-grants-2014_02
Patent number
US08658681B2

Reaction notes

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