November 27, 2024, 04:40:39 PM
Forum Rules: Read This Before Posting


Topic: Reduction of nitro compound  (Read 1985 times)

0 Members and 1 Guest are viewing this topic.

Offline organicstudent

  • Very New Member
  • *
  • Posts: 1
  • Mole Snacks: +0/-0
Reduction of nitro compound
« on: April 07, 2018, 05:46:39 AM »
The question is asking how to convert the nitro compound into the product explaining the order of events with regard to reduction steps.

I have tried researching cyclisation reactions involving the reduction of NO2 but have found little to nothing. I think that the reaction has something to do with protection groups; protection of the carbonyl.

Thank you!
« Last Edit: April 07, 2018, 06:58:04 AM by Arkcon »

Offline crawlingmcedge

  • Regular Member
  • ***
  • Posts: 21
  • Mole Snacks: +5/-0
Re: Reduction of nitro compound
« Reply #1 on: April 07, 2018, 09:03:06 AM »
I would guess first reduce to the aniline first. I suppose then use SOCl2 to change to acid chloride which would give self cyclization.

Remove the carbonyl using clemmenson or wolf kishhner

Offline zsinger7

  • Regular Member
  • ***
  • Posts: 9
  • Mole Snacks: +0/-0
Re: Reduction of nitro compound
« Reply #2 on: April 07, 2018, 03:37:35 PM »
If you had "researched everything," you would know the answer!  Try the Mozingo reduction (OUTSIDE!!!!!) if you have a sensitive substrate.  Use Wolff-Kishner with acid sensitive, Clemmensen with base sensitive, or Mozingo as a last resort (trust me, Me2S is HORRIBLE STUFF!).  And as stated above, nitro must be reduced (Use tin/HCl then freebase it).

        -Zack

Offline Arkcon

  • Retired Staff
  • Sr. Member
  • *
  • Posts: 7367
  • Mole Snacks: +533/-147
Re: Reduction of nitro compound
« Reply #3 on: April 07, 2018, 06:08:20 PM »
OK, thanks to everyone for playing.  That was great.  You're beautiful, all of ya's.  :Golf Clap:

*Topic Locked*

OK, everybody, I'd like to welcome you and everyone new to the Chemical Forums,  but I want to ask you to review our Forum Rules{click}.  You already accepted the rules when you signed up for our forum, and you have to follow them, whether you agree with them or not, or even if you're unaware of them.

We don't dump complete answers on this forum, which is what each responder did.  New posters we  like to help you learn to help yourself.  The O.P. should have done more to show actual work, as well.
« Last Edit: April 15, 2018, 07:54:09 PM by Arkcon »
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Sponsored Links