Methanol → HCID 178499180, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitro-1H-pyrazole-3-carboxylic acid (2.0 g, 12.7 mmol) in dichloromethane at 25° C. was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.68 g, 14.0 mmol), methanol (8.2 mL), and 4-dimethylaminopyridine (155 mg, 1.27 mmol). The reaction was stirred at 25° C. for 18 h. At this time, the reaction was diluted with dichloromethane and was washed with a 1N aqueous hydrochloric acid solution (1×50 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 45:55 ethyl acetate/petroleum ether) afforded 4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (1.06 g, 48.8%) as a white solid: LR-MS for C5H5N3O4 (M−H)+ at m/z=170.

Provenance & Evidence