Yield:959240-93-8 94%

Reaction Conditions:

in ethanol;Reflux;regioselective reaction;

Steps:

1 General procedure for synthesis of 3-amino-1-methyl-1H-indazole 2

General procedure: A mixture of benzonitrile 1 (10.0 mmol) and methylhydrazine (2.8 mL, 50.0 mmol) in EtOH (10.0 mL) was heated to reflux overnight. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using EtOAc/hexanes (1:1) as eluent to give the product 2.

References:

Liu, Han-Jun;Hung, Shiang-Fu;Chen, Chuan-Lin;Lin, Mei-Huey [Tetrahedron,2013,vol. 69,# 19,p. 3907 - 3912]