Potassium Carbonate → 1,3-Di-tert-butyl-1H-pyrazol-5-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 12.5 g of 4,4-dimethyl-3-oxopentanenitrile, 25 g of tert-butylhydrazine hydrochloride, and 27.6 g of potassium carbonate in 400 mL of ethanol was refluxed for 24 h. The mixture was cooled to 25° C. and then it was filtered. The solvent was evaporated from the filtrate and the residue was partitioned between ethyl acetate and distilled water. The organic phase washed with brine and dried (MgSO4). The solvent was evaporated at reduced pressure and the residue was dissolved in a small volume of ether. The mixture was diluted with an equal volume of hexanes and then the volume of the solution was reduced by one half by evaporation at reduced pressure. The white solid which precipitated was collected by filtration to give 8.7 g of 5-Amino-1,3-di(tert-butyl)pyrazole 17. 1H-NMR (CDCl3): δ 5.43 (s, 1H), 1.62 (s, 9H), 1.25 (s, 9H).

Provenance & Evidence