Dichloromethane → 1-(p-Chlorobenzyl)-1-[4-(quinolin-2-ylmethoxy)phenyl]hydrazine

Participants

Reaction Steps

A quantity of 10 g of 4-(quinolin-2-ylmethoxy)phenylhydrazine from Step C was added to a solution of 10.5 mL of diisopropylethylamine and 150 mL of CH2Cl2. To the yellow suspension was added 9.11 g of p-chlorobenzyl chloride followed by 3.64 g of Bu4NBr and 50 mL of CH2Cl2. The reaction was stirred for approximately 24 hours. When no starting material remained, the reaction was diluted with H2O and extracted 3 times with CH2Cl2. The combined organic phase was washed once with water and dried (MgSO4), filtered and evaporated to dryness. The solid residue was dried under vacuum overnight prior to being swished in ether/methanol 90/10 to give the title compound as a pale yellow solid. m.p. 130° C.

Provenance & Evidence