4-(Azidomethyl)benzonitrile → 4-(Aminomethyl)benzonitrile

HRID 1263426Notes

Reaction equation

HRID 1263426 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=1)=[N+]=[N-]>CCOC(C)=O.[Pd]>[C:4]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1)#[N:1]

Participants

4

Reactant 1

HCID 110736914-(Azidomethyl)benzonitrile2×

Product 1

HCID 826084-(Aminomethyl)benzonitrileYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Pd-on-C (Aldrich, 800 mg) catalyst was added to a solution of α-azido-4-cyanotoluene (compound 33, 8 g, 51 mmol) in EtOAc (150 mL). The reaction mixture was hydrogenated (H2, 45 psi) in a Parr apparatus for 11 hours. Catalyst was removed by filtering and the solvent was removed under vacuum to give the title compound (6.3 g, 93%). 1HNMR (CDCl3) δ3.85 (s, 2H), 7.45 (d, 2H, J=8.1), 7.60 (d, 2H, J=8.1 Hz), 7.78 (s, 2H, NH2).

Workup

  1. customfor 11 hours
  2. customCatalyst was removed
  3. filtrationby filtering
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-591430030c1d44d998cd4a105a6b45fb
Source dataset
uspto-grants-2003_04
Patent number
US06541467B1

Reaction notes

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