Water → N-(4-Methoxybenzyl)-N-methylhydrazine

Participants

Reaction Steps

Tetrahydrofuran (40 ml) was added to lithium aluminumhydride (1.94 g), the mixture was heated and stirred gently under an argon atmosphere, and a solution (10 ml) of 4-methoxybenzoic acid N-methyl hydrazide (4.78 g) prepared in the Step 14-1-1 in THF was added thereto. The resulting mixture was further stirred for 15 hours under heat reflux. The mixture was allowed to cool to a room temperature, and then water (2 ml) and a 1-N sodium hydroxide aqueous solution (7.5 ml) were added dropwise to the mixture. The reaction solution was filtered through a celite, and the filtrate was concentrated under a reduced pressure. The concentrate was purified by silica gel column chromatography (dichloromethane:methanol=50:1) to give the title compound (2.27 g, 45%).

Provenance & Evidence