Sciencemadness Discussion Board

Reductive amination with zinc Zn

seba - 21-6-2013 at 19:34

Has anyone tried reductive amination with zinc?

Article: http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170205/

sonogashira - 21-6-2013 at 23:21

Giovanni B Giovenzana, Daniela Imperio, Andrea Penoni, and Giovanni Palmisano.

seba - 22-6-2013 at 08:09

An another relevant publication:
http://www.sciencedirect.com/science/article/pii/S0040403998...

I have the full PDF. It works also with ketones and ammonia, not just aldehydes and primary amines. But this article is with imines, not imines created in-situ.

Would be great if it worked

hive3 - 3-7-2013 at 07:54

This is a very green solution that can replace some very dangerous chemicals typically used in this process. Be very careful with what you run through this rxn as you might end up with a very illegal substance.

See Also

hive3 - 3-7-2013 at 08:52

Reductive methylation of primary and secondary amines and
amino acids by aqueous formaldehyde and zinc Renato A. da Silva,a Ida´lia H. S. Estevamb and Lothar W. Biebera,* (2007)

:)



seba - 4-7-2013 at 06:37

I've tried acetone + ammonia + Zn/NaOH and I think it works. The smell is different, fishy.

[Edited on 4-7-2013 by seba]

ElectroWin - 16-7-2013 at 18:36

any idea of the yield?

Mush - 7-9-2014 at 03:44

Quote: Originally posted by ElectroWin  
any idea of the yield?


Could be quite high. It depends on the reaction conditions.

Reductive methylation of primary and secondary amines and amino acids by aqueous formaldehyde and zinc
Renato A. da Silva, Idalia H. S. Estevam and Lothar W. Bieber
Tetrahedron Letters 48 (2007), 7680-7682




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Mush - 7-9-2014 at 03:51

Quote: Originally posted by seba  
An another relevant publication:
http://www.sciencedirect.com/science/article/pii/S0040403998...

I have the full PDF. It works also with ketones and ammonia, not just aldehydes and primary amines. But this article is with imines, not imines created in-situ.


Organic reaction in water. Part 1. A convenient method for reduction of imines using zinc powder

Takehito Tsukinokia, Yoshiharu Mitomaa, Satoko Nagashimaa, Takatoshi Kawaji†, Iwao Hashimoto†,Masashi Tashiroa

Tetrahedron Letters
Volume 39, Issue 48, 26 November 1998, Pages 8873–8876

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