Ammonium Chloride → 5-Amino-2-[1,2,4]triazol-1-ylbenzonitrile

Reaction equation

[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10])([O-])=O.[Cl-].[NH4+].[In]>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

Participants

Procedure

5-Nitro-2-[1,2,4]triazol-1-yl-benzonitrile (1.14 g, 5.3 mmol) was dissolved in ethanol (23 mL) and satd. aq. ammonium chloride (5.3 mL) before adding indium powder (3.25 g, 28.2 mmol). The mixture was then refluxed for 3 h, cooled to RT, and the solids filtered (MeOH washed). The filtrate was diluted with water, basified with 1N NaOH (aq), and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated under vacuum to yield the title compound (0.88 g). MS (ESI+) for m/z 186 (M+H)+.