4-Nitrobenzyl chloride → HCID 20086966, compound

Participants

Reaction Steps

4.5 g (15 mmoles) of 4,5-dichloro-2-(4-nitrobenzyl)-3(2H)-pyridazinone (prepared according to method III but using 4-nitrobenzyl chloride instead of 3-phenyl-2-propenyl chloride (M.P. 128-130 celsius)) are dissolved in 150 ml of 99.5% acetic acid solution. Then 7.5 g of iron dust are added to the solution at such a rate that the temperature should not exceed 20° C., and the suspension is stirred at room temperature for 8 hours. By working up the reaction mixture in the usual manner 3.15 g (77%) of 2-(4-aminobenzyl)-4,5-dichloro-3(2H)-pyridazinone melting at 187°-189° C. are obtained, which is dissolved in 34 ml of anhydrous pyridine. To the solution 1.24 ml (16 moles) of methanesulfonyl chloride are dropped under stirring and cooling at such a rate that the inner temperature should remain between 0° C. and 5° C. The mixture is then stirred at room temperature for 4 hours and poured onto water. The separated crystals are filtered and washed with water. Thus 2.34 g (57%) of the desired compound are obtained. M.p.: 152°-154° C.

Provenance & Evidence