fpshacker

I am attempting to synthesis 4,5-dimethoxy-1,2-diaminobenzene from 4,5-dimethoxyveratrole. To do this, I have attempted reductions with Sn and Zn in acid solutions. These reactions produce the desired product and have no side reactions; NMR shows no other organic products.

The problem is, when I do the basic workup I run into some sort of trouble. The product I get is a heterogeneous mix of discolored (dark purple almost black) solid mixed with white crystals. When doing the basic workup for both Zn and Sn reductions, the solution turns black when it becomes basic. I have no clue what this black crap is, but it is soluble in both the aqueous and organic solvents. I've tried to remove it by