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

HRID 554244Notes

Reaction equation

HRID 554244 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]>CO.[C].[Pd]>[NH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1

Participants

4

Reactant 1

HCID 27590482-Fluoro-4-nitrobenzonitrile

Product 1

HCID 27834134-Amino-2-fluorobenzonitrileYield 70%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-fluoro-4-nitrobenzonitrile (2.51 g) in methanol (125 mL) was added 10% palladium carbon (50% containing water, 237 mg), and the mixture was stirred under a hydrogen atmosphere for 3 hr. The reaction mixture was filtrated, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1) to give the title compound as a pale-yellow solid (yield 1.43 g, 70%).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by basic silica gel column chromatography (eluent: hexane-ethyl acetate=1:1)

Sources & evidence

ORD record
ord-3d02239a01fd42c9855500b64cd29d63
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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