Ammonia → 3,5-Difluorobenzylamine

HRID 1722721Notes

Reaction equation

HRID 1722721 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].N>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5872043,5-Difluorobenzonitrile

Product 1

HCID 1452113,5-DifluorobenzylamineYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 3,5-difluorobenzonitrile (4 g, 28.8 mmole) in methanol saturated with ammonia (100 ml) was added to a slurry of methanol washed Raney nickel. The mixture was shaken under 50 psi hydrogen for 1.5 hours, filtered and the filtrate evaporated. The residue was dissolved in ethyl acetate and extracted with 3N HCl. The acidic solution was basified with 50% sodium hydroxide and was extracted into ethyl acetate. The organic extract was dried (Na2SO4) and concentrated to give 3.0 g (74%) of title compound as a yellow oil which was stored under nitrogen.

Workup

  1. washwashed Raney nickel
  2. filtrationfiltered
  3. customthe filtrate evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with 3N HCl
  6. extractionwas extracted into ethyl acetate
  7. extractionThe organic extract
  8. dry with materialwas dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-48074ea3e6cd4d8bb80c99663b49d544
Source dataset
uspto-grants-1989_08
Patent number
US04857540

Reaction notes

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