2-Fluoro-4-nitrobenzonitrile → 4-Amino-2-fluorobenzonitrile

HRID 1927374Notes

Reaction equation

HRID 1927374 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.C(OCC)(=O)C.[Fe]>[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 1

HCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 27834134-Amino-2-fluorobenzonitrileYield 96%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-nitro-2-fluorobenzonitrile (1.83 g, 5 mmol) and iron (1.68 g, 6 mmol) in 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-7ca473f2d6ec41cbb06cf6ade2636503
Source dataset
uspto-grants-2012_05
Patent number
US08183274B2

Reaction notes

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