3,5-Difluorobenzonitrile → 3,5-Difluorobenzylamine

HRID 1193589Notes

Reaction equation

HRID 1193589 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[C:5]#[N:6].[H][H]>N.CO.[Ni]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH2:5][NH2:6]

Participants

6

Reactant 2

HCID 5872043,5-DifluorobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 1452113,5-DifluorobenzylamineYield 87.1%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of 3,5-difluorobenzonitrile (0.0345 mol) in ammonia saturated methanol (100 ml) and methanol washed Raney nickel were shaken together under 50 psi of hydrogen for 11/2 hours. The reaction mixture was filtered, the filtrate concentrated then dissolved in ethyl acetate. The product was extracted into 3N aqueous hydrogen chloride. The acidic solution was cooled and basified with 50% sodium hydroxide then was extracted into ethyl acetate. The organic extract was dried over sodium sulfate, filtered and concentrated to yield 4.3 g (86%) yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. dissolutionthen dissolved in ethyl acetate
  4. extractionThe product was extracted into 3N aqueous hydrogen chloride
  5. temperatureThe acidic solution was cooled
  6. extractionthen was extracted into ethyl acetate
  7. extractionThe organic extract
  8. dry with materialwas dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-aced0f48405f4c1aa87866517f78a83e
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

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