Acetic Acid → N-Benzyl-2,4-difluoroaniline

HRID 1461569Notes

Reaction equation

HRID 1461569 reaction equation
[CH:1](=[N:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>O1CCCC1.[Ni]>[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 12129977HCID 12129977, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22667090N-Benzyl-2,4-difluoroaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

195.4 g (0.9 mol) of N-benzal-2,4-difluoroaniline are dissolved in 900 ml of tetrahydrofuran in an autoclave. 19 g of Raney nickel and 2 g of acetic acid are added, and the mixture is hydrogenated at 60° to 85° C. and a hydrogen pressure of 100 bar. The end point of the reaction is determined by thin-layer chromatography or gas chromatography. The suspension is filtered and the solution is evaporated on a vacuum rotary evaporator. The residue is distilled in vacuo at 102° C. and 3.6 mbar, to give 125.6 g (64% of theory) of a pale yellow liquid.

Workup

  1. customis hydrogenated at 60° to 85° C.
  2. filtrationThe suspension is filtered
  3. customthe solution is evaporated on a vacuum rotary evaporator
  4. distillationThe residue is distilled in vacuo at 102° C.
  5. custom3.6 mbar, to give 125.6 g (64% of theory) of a pale yellow liquid

Sources & evidence

ORD record
ord-e1d45da36b08465eb700c6ccbac00004
Source dataset
uspto-grants-1991_12
Patent number
US05075467

Reaction notes

Loading…