Ammonium Chloride → 1-benzyl-1H-indazol-4-amine

Participants

Reaction Steps

A mixture of 1-benzyl-4-nitro-1H-indazole (150 mg; 0.592 mmol), iron powder (331 mg; 5.92 mmol) and ammonium chloride (16 mg; 0.296 mmol) in ethanol/water (4:1; 5 mL) was heated at reflux for 5 hours. The solvent was removed under vacuum and the residue was mixed with ethyl acetate/triethylamine (4:1; 5 mL) and heated at reflux for 1 hour. The mixture was allowed to cool and then filtered through a pad of silica, washing with ethyl acetate. The solvent was removed under vacuum to give the desired product that was used directly in the next step.

Provenance & Evidence