Chlorosuccinimide → 6-amino-5-chloro-1H-indazole-7-carboxylic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1.66 g (8.71 mmol) of 6-amino-1H-indazole-7-carboxylic acid methyl ester in 17 mL of N,N-dimethylformamide, is added 1.21 g (8.71 mmol) of N-chlorosuccinimide. The mixture is stirred during 4 hours at 50° C. and then the solvent is evaporated. The residue is precipitated in ethyl acetate and after filtration and washings with ethyl acetate, 927 mg of a pure white solid are obtained. The filtrate is evaporated and submitted to a flash chromatography which gives an additional 723 mg of the compound. In totality, 1.65 g (84%) of a product are obtained as a white solid; LC/MS:226/228 (M+H)+.

Provenance & Evidence