2-Chloro-4-fluoro-5-nitrobenzyl cyanide → 2-(5-Amino-2-chloro-4-fluorophenyl)acetonitrile

HRID 1709777Notes

Reaction equation

HRID 1709777 reaction equation
[H][H].[Cl:3][C:4]1[CH:12]=[C:11]([F:13])[C:10]([N+:14]([O-])=O)=[CH:9][C:5]=1[CH2:6][C:7]#[N:8]>[Ni].C(O)C>[NH2:14][C:10]1[C:11]([F:13])=[CH:12][C:4]([Cl:3])=[C:5]([CH:9]=1)[CH2:6][C:7]#[N:8]

Participants

5

Reactant 2

HCID 230367452-Chloro-4-fluoro-5-nitrobenzyl cyanideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 230367472-(5-Amino-2-chloro-4-fluorophenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Hydrogen is injected at 25°-30° C., under normal pressure, into a mixture consisting of 8.9 g of 2-chloro-4-fluoro-5-nitrobenzyl cyanide, 1 g of Raney nickel in 90 ml of absolute ethanol, until the stoichiometric amount of hydrogen has been absorbed. After completion of the absorption of hydrogen, the reaction mixture is filtered and the alkaline filtrate is concentrated by evaporation. The residue consists of 7.5 g of 5-amino-2-chloro-4-fluorobenzyl cyanide having a melting point of 85°-86° C.

Workup

  1. customis injected at 25°-30° C., under normal pressure, into a mixture
  2. customhas been absorbed
  3. customAfter completion of the absorption of hydrogen
  4. filtrationthe reaction mixture is filtered
  5. concentrationthe alkaline filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-bcfdc784943f4c81ac6b0e8dd9478f94
Source dataset
uspto-grants-1990_08
Patent number
US04950777

Reaction notes

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