Hydrochloric Acid → 1-[2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine hydrochloride

HRID 1664151Notes

Reaction equation

HRID 1664151 reaction equation
[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8]#[N:9])[CH:5]=[N:4][CH:3]=[N:2]1.[ClH:14]>C(O)C.[Pd]>[ClH:14].[N:1]1([C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[CH2:8][NH2:9])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 157121632-(1H-1,2,4-triazol-1-yl)Benzonitrile

Product 1

HCID 210697781-[2-(1H-1,2,4-triazol-1-yl)phenyl]methanamine hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(1H-1,2,4-Triazol-1-yl)benzonitrile (4.25 g, 25 mmol) was dissolved in ethanol (50 mL) and 1N HCl (25 mL). 10% Pd—C (1 g) was added and the mixture shaken under H2 for 2 h at 50 psi. After filtration through Celite® and concentration, the residue was triturated with diethyl ether and the title compound was collected as a white solid. (3.94 g, 75% yield). 1H-NMR (300 MHz, CD3OD) δ ppm: 9.01 (1H, s), 8.32 (1H, s), 7.78-7.64 (4H, m), 4.15 (2H, s). LCMS [M+H]+ calcd for C9H11N4: 175.09; found: 175.17.

Workup

  1. filtrationAfter filtration
  2. concentrationthrough Celite® and concentration
  3. customthe residue was triturated with diethyl ether
  4. customthe title compound was collected as a white solid

Sources & evidence

ORD record
ord-3dd60c9645164d5fa40e0245f6a79130
Source dataset
uspto-grants-2011_10
Patent number
US08039458B2

Reaction notes

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