4-Chlorobenzonitrile → 4-Chlorobenzylamine

HRID 1045040Notes

Reaction equation

HRID 1045040 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[H][H]>N.CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 121634-ChlorobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 660364-ChlorobenzylamineYield 91.8%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Activated Ni EnCat (0.26 g, water wet, 20 mol % Ni on substrate) was washed with MeOH three times to remove water and added to 4-chlorobenzonitrile (0.137 g, 1 mmol) dissolved in 7 N ammonia in MeOH (4 ml) in a pressure vessel. The vessel was sealed and purged twice with hydrogen then pressurised to 5-6 bar with hydrogen and the contents magnetically stirred at room temperature. Progress of reaction was carried out by GCMS analysis. After 24 h the hydrogen was vented and the Ni EnCat beads removed by filtration. The filtrate was concentrated on a rotary evaporator to give 4-chlorobenzylamine (0.13 g, 91%). GCMS purity 77%.

Workup

  1. washActivated Ni EnCat (0.26 g, water wet, 20 mol % Ni on substrate) was washed with MeOH three times
  2. customto remove water
  3. customThe vessel was sealed
  4. custompurged twice with hydrogen
  5. customProgress of reaction
  6. customthe Ni EnCat beads removed by filtration
  7. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-945de9cd0f8e44a48ea4688bd624465f
Source dataset
uspto-grants-2013_10
Patent number
US08563753B2

Reaction notes

Loading…