Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: tommy1 on March 21, 2012, 06:38:41 PM

Title: Primary amine to alcohol
Post by: tommy1 on March 21, 2012, 06:38:41 PM

I am having trouble coming up with conditions to give me the best yield of the product I want.
I have cyclohexamine with two ester groups in the para position and CONH2 ortho and I want to convert the amine group to the hydroxyl.

Literature has been using bases at high temperatures, but i think this will just break my esters apart. Others use NaNO3 with weak acid, but they were aiming for a product where both esters were cleaved, and I want them to remain...
 I was thinking of a Schiemann type reaction, but not sure if the esters will be affected by the halogen.
Any suggestions for conditions or methods would be greatly appreciated! :)

Title: Re: Primary amine to alcohol
Post by: discodermolide on March 22, 2012, 08:36:23 AM

Quote from: tommy1 on March 21, 2012, 06:38:41 PM

I am having trouble coming up with conditions to give me the best yield of the product I want.
I have cyclohexamine with two ester groups in the para position and CONH2 ortho and I want to convert the amine group to the hydroxyl.

Literature has been using bases at high temperatures, but i think this will just break my esters apart. Others use NaNO3 with weak acid, but they were aiming for a product where both esters were cleaved, and I want them to remain...
 I was thinking of a Schiemann type reaction, but not sure if the esters will be affected by the halogen.
Any suggestions for conditions or methods would be greatly appreciated! :)

Have a look at Tet. Letts. 1995, 36(14), 2377. "A mild oxidation of aromatic amines". They use oxone.