2-(1H-1,2,4-triazol-1-yl)Benzonitrile → [2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine

HRID 857723Notes

Reaction equation

HRID 857723 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[C:12]#[N:13])[CH:5]=[N:4][CH:3]=[N:2]1>[Pd].C(O)C>[N:1]1([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:12][NH2:13])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 157121632-(1H-1,2,4-triazol-1-yl)Benzonitrile

Product 1

HCID 4913133[2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(1,2,4-triazol-1-yl)cyanobenzene (508 mg, 2.99 mmol) and 25% by weight of palladium on carbon, 10% catalyst (134 mg) in ethanol (75 ml) was placed on a PARR Hydrogenation Apparatus under a hydrogen atmosphere at 55 psi. overnight. The mixture was filtered through celite and concentrated to give 2-(1,2,4-triazol-1-yl)-benzylamine; 1H NMR (CD3OD) δ 8.80 (s, 1H), 8.22 (s, 1H), 7.64–7.43 (m, 4H), 3.66 (s, 2H).

Workup

  1. customovernight
  2. filtrationThe mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-dd4bb516616741e38e51dc33ec9995ef
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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