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

HRID 621392Notes

Reaction equation

HRID 621392 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-7608c611ec814e72aaa4b3184c2e28d3
Source dataset
uspto-grants-1989_04
Patent number
US04824476

Reaction notes

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