Hydrochloric Acid → 4-(Pyrid-2-ylmethoxy)phenylhydrazine

Participants

Reaction Conditions

Reaction Steps

4-(Pyrid-2-ylmethoxy)aniline (86.7 g; 433 mmol), prepared as in step 2, was suspended in 200 mL water and 108 mL concentrated HCl was added. The solution was cooled to 0° C. and sodium nitrite (30.8 g; 446 mmol) in 75 mL water was added dropwise. The reaction was stirred for 1 hour at 0° C. The diazonium salt was then transferred dropwise to a solution of sodium hydrosulfite (85% purity; 487 g; 2.80 mol) in 2000 mL water, 2000 mL diethyl ether, and 20 mL 2N aqueous NaOH at 0°-5° C. with vigorous stirring. When addition was complete 775 mL 2N aqueous NaOH was added dropwise. The cooling bath was removed and the reaction was stirred at room temperature for 1 hour. The precipitate was collected by vacuum filtration and washed with water then diethyl ether. The reaction yielded 4-(pyrid-2-ylmethoxy)phenylhydrazine as a pale green solid.

Provenance & Evidence