Potassium Carbonate → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

Participants

Reaction Steps

A mixture of 4-methoxyphenylhydrazine hydrochloride (459 g, 2.63 mol), 4-bromobenzyl bromide (715 g, 2.86 mol) and milled potassium carbonate (771 g, 5.58 mol) was suspended in 2 L DMF at 0° C. with overhead stirring. The ice bath was removed and the mixture was stirred for 4 h, then diluted with 15 L of ice water. The mixture was stirred vigorously for 1 h, then the aqueous layer was decanted from the gummy solid. The solid was washed with 2×4 L of water, then was dissolved in 2.5 L toluene and dried over Na2SO4. The mixture was filtered, and the filtrate was cooled in an ice bath and treated with a stream of HCl gas for 1 h with vigourous stirring. The precipitate was filtered and washed with 3×0.5 L of cold toluene and dried under a stream of nitrogen to give 682 g of the title compound.

Provenance & Evidence