Hydrochloric Acid → 4-Cyano-2,5-difluorobenzylamine

HRID 1717504Notes

Reaction equation

HRID 1717504 reaction equation
[BH4-].[Na+].[N:3]([CH2:6][C:7]1[C:14]([F:15])=[CH:13][C:10]([C:11]#[N:12])=[C:9]([F:16])[CH:8]=1)=[N+]=[N-].Cl>O.C1COCC1.[Pd]>[NH2:12][CH2:11][C:10]1[C:9]([F:16])=[CH:8][C:7]([C:6]#[N:3])=[C:14]([F:15])[CH:13]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 219046104-Azidomethyl-2,5-difluorobenzonitrile

Product 1

HCID 219046324-Cyano-2,5-difluorobenzylamine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

This reaction was carried out according to the procedure described in J. Chem. Res. (M) (1992) 3128. To a suspension of 300 mg of 10% Pd/C (50% moisture) in 20 mL of water was added a solution of sodium borohydride (0.779 g, 0.0206 mol) in 20 mL of water. Some gas evolution resulted. 4-Azidomethyl-2,5-difluorobenzonitrile (1.00 g, 5.15 mmol; from step (v) above) was dissolved in 60 mL of THF and added to the aqueous mixture on an ice bath. The mixture was stirred for 1.5 h whereafter 10 mL of 2M HCl was added and the mixture was filtered through Celite. The Celite was rinsed with more water and the combined aqueous phase was washed with EtOAc and subsequently made alkaline with 2M NaOH. Extraction three times with methylene chloride followed and the combined organic phase washed with water, dried (Na2SO4) and evaporated. Yield: 0.47 g (54%).

Workup

  1. customSome gas evolution resulted
  2. additionadded to the aqueous mixture on an ice bath
  3. additionwas added
  4. filtrationthe mixture was filtered through Celite
  5. washThe Celite was rinsed with more water
  6. washthe combined aqueous phase was washed with EtOAc and subsequently made alkaline with 2M NaOH
  7. extractionExtraction three times with methylene chloride
  8. washthe combined organic phase washed with water
  9. dry with materialdried (Na2SO4)
  10. customevaporated

Sources & evidence

ORD record
ord-f7452a3146724f48b1b5defd93f0daa8
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

Loading…