4-[1-(1-Imidazolyl)-butyl]-benzonitrile → 4-[1-(1-Imidazolyl)butyl]-benzaldehyde

HRID 727848Notes

Reaction equation

HRID 727848 reaction equation
[N:1]1([CH:6]([C:10]2[CH:17]=[CH:16][C:13]([C:14]#N)=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.C(O)=[O:19].O>[Al].[Ni]>[N:1]1([CH:6]([C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:19])=[CH:12][CH:11]=2)[CH2:7][CH2:8][CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 145143624-[1-(1-Imidazolyl)-butyl]-benzonitrileHCID 18673298Formic acid--water (1/1)

Product 1

HCID 145143774-[1-(1-Imidazolyl)butyl]-benzaldehyde

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Procedure

10 g of nitrile of example 4 is refluxed with 10 g of aluminum nickel alloy in 150 ml of formic acid/water (75:25) for 1 hour. It is filtered on kieselguhr, the filtrate is alkalized with solid potassium carbonate, 100 ml of aqueous ammonia is added and extracted with ether. After drying and concentration by evaporation of the ether, it is distilled on a bulb tube; 9.1 g of 4-[1-(1-imidazolyl)butyl]-benzaldehyde is obtained, melting 200° C./0.03 mbar.

Workup

  1. filtrationIt is filtered on kieselguhr
  2. additionis added
  3. extractionextracted with ether
  4. customAfter drying
  5. concentrationconcentration
  6. customby evaporation of the ether, it
  7. distillationis distilled on a bulb tube

Sources & evidence

ORD record
ord-a1e772603d33436ba04f83519ca41b85
Source dataset
uspto-grants-1991_09
Patent number
US05045558

Reaction notes

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