Methylhydrazine → 5-amino-1-methyl-N-(1-methylethyl)-1H-pyrazole-4-carboxamide

Participants

Reaction Conditions

Reaction Steps

1.0 g (8.0 mmol) of 2-cyano-N-(1-methylethyl)acetamide (prepared according to the procedure of Cheikh et al J. Org. Chem., 1991, 56, 970) was combined with 3.1 mL of triethylorthoformate, 5 mL of acetic anhydride and 0.01 g of anhydrous zinc chloride. The mixture was refluxed for 1 hour. A distillation head was placed on the flask and the reaction was heated at 120° C. for 8 hours. After standing for two days the mixture was heated again for 12 hours at 120° C. for 12 hours. The volatiles were removed with a rotary evaporator. Ethanol was added and the volatiles were again removed with a rotary evaporator. This material was dissolved in 15 mL of ethanol. 0.34 mL (6.4 mmol) of methyl hydrazine was added. The reaction mixture was refluxed for 5 hours and then allowed to stand at room temperature overnight. The solvent was removed with a rotary evaporator. The residue was purified by MPLC (ethyl acetate as eluant) to afford 0.14 g of the title compound as a solid.

Provenance & Evidence