2,6-Dichloro-3-fluoro-5-nitrobenzonitrile → 3-Cyano-2,4-dichloro-5-fluoroaniline

HRID 47905Notes

Reaction equation

HRID 47905 reaction equation
[C:1]([C:3]1[C:4]([Cl:14])=[C:5]([N+:11]([O-])=O)[CH:6]=[C:7]([F:10])[C:8]=1[Cl:9])#[N:2].[H][H]>[Pd].C(O)C>[C:1]([C:3]1[C:4]([Cl:14])=[C:5]([CH:6]=[C:7]([F:10])[C:8]=1[Cl:9])[NH2:11])#[N:2]

Participants

5

Reactant 2

HCID 234317952,6-Dichloro-3-fluoro-5-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 234317783-Cyano-2,4-dichloro-5-fluoroaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

27.0 g of 3-cyano-2,4-dichloro-5-fluoronitrobenzene (0.247 mol), 500 ml of ethanol and 2.18 g of Pd/C were heated to 60° C. and hydrogenated under 3 Mpa of hydrogen pressure for 3 hours. The reaction mixture was cooled to room temperature. The catalyst was filtered off. After removing the solvent, 48.0 g of 3-cyano-2,4-dichloro-5-fluoroaniline were given in 94.7 yield.

Workup

  1. filtrationThe catalyst was filtered off
  2. customAfter removing the solvent, 48.0 g of 3-cyano-2,4-dichloro-5-fluoroaniline
  3. customyield

Sources & evidence

ORD record
ord-4bc98b06321d4f47a6ecc41e0e945a1c
Source dataset
uspto-grants-2004_03
Patent number
US06699992B2

Reaction notes

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