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

HRID 346171Notes

Reaction equation

HRID 346171 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]>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

4

Reactant 1

HCID 855042-Chloro-5-nitrobenzonitrile

Product 1

HCID 109972345-Amino-2-chlorobenzonitrileYield 43.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 10.0 g (54.8 mmol) 2-chloro-5-nitrobenzonitril in 500 ml ethanol was hydrogenated at 40 psi by using 0.5 g 5% Pd-C as a catalyst. The catalyst was filtered off and the filtrate was evaporated in vacuo. Recrystallization (ethanol-water) gave 3.6 g (43%) 5-amino-2-chlorobenzonitril. M.p. 129-130° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. customRecrystallization (ethanol-water)

Sources & evidence

ORD record
ord-1cbba4641d134b3d8e723ba4bf254661
Source dataset
uspto-grants-1991_10
Patent number
US05061706

Reaction notes

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