Toluene → N-(p-Bromobenzyl)-N-(4-methoxyphenyl)hydrazine hydrochloride

Participants

Reaction Conditions

Reaction Steps

4-Methoxyphenylhydrazine hydrochloride (1.0 eq) was added to a reaction flask containing toluene (16.5-fold, V/W of starting material) under N2. 4-Bromobenzyl bromide (1.05 eq) and triethylamine (2.1 eq) were added, and the mixture was heated to 100-105° C. and stirred for 3 hours. The reaction was then cooled to room temperature and checked by analytical thin layer chromatography (tlc) for completion. Since no starting material was seen by tlc analysis, the reaction was diluted with ethyl acetate (10.0-fold, V/W of starting material) and agitated for 1.5 hours. The mixture was filtered to collect the solid product, which was subsequently washed with toluene and dried under vacuum at 60-65° C. Ethyl acetate (10.0-fold, V/W of starting material) was then added to the product and the mixture was agitated well. The pH of the solution was adjusted to pH 2 with saturated hydrochloric acid/ethyl acetate solution and further agitated for 1 hour. The solid was then collected by filtration, washed with cold ethyl acetate, and air dried. The product was taken on to the next step without further purification.

Provenance & Evidence