Chemical Properties
Brown Solid
Uses
4-(1H-1,2,4-Triazol-1-ylmethyl)benzenamine is an intermediate useful in organic synthesis and other chemical processes.
Uses
Rizatriptan intermediate
Synthesis
General procedure for the synthesis of 4-[1H-1,2,4-triazol-1-ylmethyl]aniline from 1-(4-nitrophenyl)methyl-1,2,4-triazole: 1-(4-nitrophenyl)methyl-1,2,4-triazole (10.0 g, 49 mmol) was dissolved in a mixed solvent of ethanol (50 ml) and ethyl acetate (50 ml), 5N HCl (10 ml) and water (1 g). The hydrogenation reaction was carried out in a Parr hydrogenation unit at 40 psi hydrogen pressure using 10% Pd/C catalyst (1.0 g) until the hydrogen uptake reached 188 psi (about 10 min). Upon completion of the reaction, the catalyst was removed by Hyflo filtration and the solvent was removed by concentration under vacuum. The residue was azeotroped twice with ethanol to afford the target product 1-(4-aminophenyl)methyl-1,2,4-triazole hydrochloride (10.6 g, 100%). The product was confirmed by NMR hydrogen spectrum (360 MHz, D2O): δ 5.53 (2H, s, CH2), 7.37-7.48 (4H, m, Ar-H), 8.12 (1H, s, Ar-H), 8.66 (1H, s, Ar-H).
References
[1] Patent: US5567726, 1996, A
[2] Patent: US5298520, 1994, A
[3] Farmaco, 1989, vol. 44, # 9, p. 831 - 841
[4] European Journal of Medicinal Chemistry, 1989, vol. 24, # 5, p. 537 - 540
[5] Patent: US5567819, 1996, A
