ORGLIST:RE: Everybody digest, Vol 2 #64 - 1 msg

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From: Rhone K. Akee (Contr) (akee$##$ncifcrf.gov)
Date: Mon May 17 2004 - 13:06:00 EDT


I used Zinc/Ammonium Formate/Methanol with 3-nitro-cinnamic and this reagent
gave me good yields without reducing the double bond. Place Compound (1eq)
and zinc (3eq, HCl acid washed, then methanol washed) in the reaction flask.
While stirring the reaction flask, slowly add ammonium formate (3eq).
Reaction should be done within 2hrs, monitor by TLC or better yet HPLC.
Need reference? Just Ask.

Mr. Rhone K. Akee
Research Associate
Natural Products Support Group, Contractor - SAIC-Frederick National Cancer
Institute
1050 Boyles Street
P.O. Box B, Bldg. 431/202
Frederick, MD 21702

Phone: (301) 846-7278
FAX: (301) 846-5206
Email: akee$##$mail.ncifcrf.gov

  

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Subject: Everybody digest, Vol 2 #64 - 1 msg

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Today's Topics:

   1. Re: Nitrogroup reduction (rajkn)

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Message: 1
Date: Sun, 09 May 2004 19:52:24 +0530
From: rajkn <rajkn_51$##$sancharnet.in>
Subject: Re: ORGLIST:Nitrogroup reduction
To: everybody$##$lists2.orglist.net

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5 or 10 % Pd-C and cyclohexene
as H donor-cum-solvent
is a mild t-BOC compatible
alternative.
Reflux follow rexn by tlc
Prof KN Rajasekharan
Unic Kerala
India
  ----- Original Message -----
  From: Maringanti Krishna
  To: everybody$##$orglist.net
  Sent: Thursday, May 06, 2004 6:19 PM
  Subject: ORGLIST:Nitrogroup reduction

  Hi All:
  I need to reduce an aromatic nitro group to -NH2. It is a large molecule
and I have an Acetal and t-BOC protections elsewhere. I have tried the
following methods.
  1. Raney Nickel, Hydrogenation: Several spots on TLC (after complete
disappearance of starting material, and after 48 hours)
  2. Pd/C Hydrogenation...very low yield after 48 hours
  3. Pd/C hydrazine hydrate. Reaction is OK but, the yield is verylow.
Difficult to get pure product. Also, acetal deprotection
  4. Electrolytic iron/ ammonium acetate and ammonium chloride. Acetal
deprotection is occuring. At rt. reaction is extremely sluggish. At reflux,
acetal deprotection is taking place.

  Can someone suggest an alternative method?
  Krishna

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<!DOCTYPE HTML PUBLIC "-//W3C//DTD HTML 4.0 Transitional//EN"> <HTML><HEAD> <META content="text/html; charset=iso-8859-1" http-equiv=Content-Type> <META content="MSHTML 5.00.2614.3500" name=GENERATOR> <STYLE></STYLE> </HEAD> <BODY bgColor=#ffffff> <DIV>5 or 10 % Pd-C and cyclohexene </DIV> <DIV>as H donor-cum-solvent</DIV> <DIV>is a mild t-BOC compatible</DIV> <DIV>alternative.</DIV> <DIV>Reflux&nbsp;follow rexn by tlc</DIV> <DIV>Prof KN Rajasekharan</DIV> <DIV>Unic Kerala </DIV> <DIV>India</DIV> <BLOCKQUOTE style="BORDER-LEFT: #000000 2px solid; MARGIN-LEFT: 5px; MARGIN-RIGHT: 0px; PADDING-LEFT: 5px; PADDING-RIGHT: 0px"> <DIV style="FONT: 10pt arial">----- Original Message ----- </DIV> <DIV style="BACKGROUND: #e4e4e4; FONT: 10pt arial; font-color: black"><B>From:</B> <A href="mailto:maringanti9$##$yahoo.com" title=maringanti9$##$yahoo.com>Maringanti Krishna</A> </DIV> <DIV style="FONT: 10pt arial"><B>To:</B> <A href="mailto:everybody$##$orglist.net" title=everybody$##$orglist.net>everybody$##$orglist.net</A> </DIV> <DIV style="FONT: 10pt arial"><B>Sent:</B> Thursday, May 06, 2004 6:19 PM</DIV> <DIV style="FONT: 10pt arial"><B>Subject:</B> ORGLIST:Nitrogroup reduction</DIV> <DIV><BR></DIV> <DIV>Hi All:</DIV> <DIV>I need to reduce an aromatic nitro group to -NH2. It is a large molecule and I have an Acetal and t-BOC protections elsewhere. I have tried the following methods.</DIV> <DIV>1. Raney Nickel, Hydrogenation:&nbsp; Several spots on TLC (after complete disappearance of starting material, and after 48 hours)</DIV> <DIV>2. Pd/C Hydrogenation...very low yield after 48 hours</DIV> <DIV>3. Pd/C hydrazine hydrate. Reaction is OK but, the yield is&nbsp; verylow. Difficult to get pure product. Also, acetal deprotection</DIV> <DIV>4. Electrolytic iron/ ammonium acetate and ammonium chloride. Acetal deprotection is occuring. At rt. reaction is extremely sluggish. At reflux, acetal deprotection is taking place.</DIV> <DIV>&nbsp;</DIV> <DIV>Can someone suggest an alternative method?</DIV> <DIV>Krishna</DIV> <P> <HR SIZE=1> <FONT face=arial size=-1>Do you Yahoo!?<BR><A href="http://pa.yahoo.com/*http://us.rd.yahoo.com/hotjobs/hotjobs_mail_signa ture_footer_textlink/evt=23983/*http://hotjobs.sweepstakes.yahoo.com/careerm akeover">Win a $20,000 Career Makeover at Yahoo! HotJobs </A></FONT></BLOCKQUOTE></BODY></HTML>

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