2-(4-Chlorophenylmethylamino)-5-fluoronitrobenzene → 2-(4-Chlorobenzylamino)-5-fluoroaniline

HRID 653665Notes

Reaction equation

HRID 653665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:4][CH:3]=1>O1CCCC1.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[NH2:17])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 149529762-(4-Chlorophenylmethylamino)-5-fluoronitrobenzene

Product 1

HCID 149529912-(4-Chlorobenzylamino)-5-fluoroanilineYield 91.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

41.7 g of 2-(4-chlorophenylmethylamino)-5-fluoronitrobenzene, prepared in Example 1, are dissolved in 1 l of tetrahydrofuran and hydrogenated at ordinary temperature and pressure in the presence of 5 g of Raney nickel. When the theoretical amount of hydrogen has been absorbed, the catalyst is filtered off and the solvent is evaporated off under vacuum to give 34.1 g of 2-(4-chlorophenylmethylamino)-5-fluoroaniline in the form of crystals melting at 99° C.

Workup

  1. customWhen the theoretical amount of hydrogen has been absorbed
  2. filtrationthe catalyst is filtered off
  3. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-9ff440c34b6b4fd8877eb13a20799d85
Source dataset
uspto-grants-1992_07
Patent number
US05128359

Reaction notes

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