Topic: How do pyruvate and hydrazine react? (Read 5309 times)

joyb · « **on:** March 03, 2013, 07:50:48 AM »

Can anyone tell me or show me what happens?

discodermolide · « **Reply #1 on:** March 03, 2013, 07:54:00 AM »

What derivatives of ketones do you know about?

joyb · « **Reply #2 on:** March 03, 2013, 08:02:09 AM »

I know hydrazine can reduce ketones to an alkane?

discodermolide · « **Reply #3 on:** March 03, 2013, 08:04:15 AM »

That's a Wolf-Kischner reduction usually needs strongly basic conditions.
What is the intermediate in that reaction?

joyb · « **Reply #4 on:** March 03, 2013, 08:07:09 AM »

An amidine? Is that it?

discodermolide · « **Reply #5 on:** March 03, 2013, 08:08:38 AM »

No it not an amidine, it has this structure:
C/C(C([O-])=O)=N/N

joyb · « **Reply #6 on:** March 03, 2013, 08:11:57 AM »

Oh yes, I'm getting my functional groups mixed up

Does nothing happen to the carboxyl group then?

discodermolide · « **Reply #7 on:** March 03, 2013, 08:13:27 AM »

You may form a hydrazine salt but as far as I am aware nothing else should happen.
So what is the functional group called?

joyb · « **Reply #8 on:** March 03, 2013, 08:28:29 AM »

A hydrazone?

discodermolide · « **Reply #9 on:** March 03, 2013, 08:30:49 AM »

Yes, it's a hydrazone.

AWK · « **Reply #10 on:** March 03, 2013, 02:41:15 PM »

Search for Fischer indole (indigo) synthesis