2-Chloro-5-nitrobenzonitrile → 5-Amino-2-chlorobenzonitrile

HRID 346134Notes

Reaction equation

HRID 346134 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][C:3]=1[C:4]#[N:5].[H][H]>C(O)C.[Pd]>[NH2:10][C:7]1[CH:8]=[CH:9][C:2]([Cl:1])=[C:3]([CH:6]=1)[C:4]#[N:5]

Participants

5

Reactant 2

HCID 855042-Chloro-5-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 109972345-Amino-2-chlorobenzonitrileYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.0 g (54.8 mmol) 2-chloro-5-nitrobenzonitrile in 500 ml ethanol was hydrogenated at 30 psi by using 0.5 g 5% Pd-C as a catalyst When the hydrogen uptake had ceased, the reaction mixture was filtered and evaporated in vacuo. The residue was recrystallized (ethanol-water) to give 3.6 g (44%) of 5-amino-2-chlorobenzonitrile. M.p. 129°-130° C.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was recrystallized (ethanol-water)

Sources & evidence

ORD record
ord-e6cde2ad305945a5a7aa2bd4def56a4c
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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