[MissPhosgene]

Oh, no, I was just wondering about how you characterized what you had as a dianion. I don't know much about that and it seems incredibly useful.

[orgopete]

I can't say we did much to characterize the dianion. There is lots of precedence. We mostly converted the dianion into the carboxylic acid, though we did other things as well.

I can say it worked really well. What I don't know is whether this is general. Can one take a simple picolinic acid amide, with an RNH, make it into a mono-anion (colorless, presumably), and then into a very colored dianion? We had multigram quantities of intermediates, derivatives, etc., we only used the derivative shown. If there was anything special about our material, solubility, etc., then it would be somewhat tedious and potentially dangerous to prep. (Post having made the stuff, an aminonitrile intermediate is quite toxic, excellent HCN delivery.)

It was really convenient. We would titrate our butyllithium in the course of doing the reactions. I thought about submitting this to Aldrich, but I never did. It also worked a lot better than the benzene analog also.