Ammonia → 2,4-Difluorobenzylamine

HRID 974387Notes

Reaction equation

HRID 974387 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H][H].N>C(O)C.[Ni]>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH2:5]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 775452,4-DifluorobenzonitrileHCID 178418361HCID 178418361, compound2×

Product 1

HCID 27332442,4-Difluorobenzylamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

13.9 g (0.10 mol) of 2,4-difluorobenzonitrile are dissolved in 100 ml of ethanol and hydrogenated in a pressurized reactor at 75°-80° C. using hydrogen gas after 1.4 g of Raney nickel in ethanol has been added and after 17 g (1.0 mol) of ammonia gas have been injected. The take-up of hydrogen is complete after about 2 hours. The reaction mixture is cooled, decompressed and filtered and then freed from solvent in a vacuum rotary evaporator. The resultant oil is subjected to fractional distillation at 70°-75° C. in vacuo (19 mbar). 9.5 g (66% of theory) of a colourless liquid are obtained.

Workup

  1. additionhas been added
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. customfreed from solvent in a vacuum rotary evaporator
  5. distillationThe resultant oil is subjected to fractional distillation at 70°-75° C. in vacuo (19 mbar)
  6. custom9.5 g (66% of theory) of a colourless liquid are obtained

Sources & evidence

ORD record
ord-72196d07537448c9a96f146a1e20c3c0
Source dataset
uspto-grants-1991_11
Patent number
US05068371

Reaction notes

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