4-Chlorobenzonitrile → 4-Chlorobenzylamine

HRID 1045042Notes

Reaction equation

HRID 1045042 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 99%

Reagents, catalysts & solvents 2

HCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

Sponge nickel from Comparative Example 1 (12 mg, 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 catalyst removed by filtration. The filtrate was concentrated on a rotary evaporator to give 4-chlorobenzylamine (0.14 g, 99%). GCMS purity 78%.

Workup

  1. washSponge nickel from Comparative Example 1 (12 mg, 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 catalyst removed by filtration
  7. concentrationThe filtrate was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-66a7e628175649f3831abbcd39d5e53f
Source dataset
uspto-grants-2013_10
Patent number
US08563753B2

Reaction notes

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