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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > June  >
In the Laboratory
Reductive Amination: A Remarkable Experiment for the Organic Laboratory
Kim M. Touchette
Bard College, Annandale-on-Hudson, NY 12504
Cover
June 2006
Vol. 83 No. 6
p. 929
Abstract
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory. The first step is a spectacular solvent-free solid-solid reaction between ortho-vanillin and para-toluidine to synthesize an imine in quantitative yield. The imine is reduced to an amine in the second step by sodium borohydride. The amine is acetylated in the third step to form the solid amide in an overall yield of 90%. The entire sequence is performed in an open beaker in less than one hour.
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Instructions for the students and notes for the instructor are available.
*  Contents JCE2006p0929W.doc (Microsoft Word)
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*  Citation
 Touchette, Kim M. J. Chem. Educ. 2006 83 929.
*  Keywords
 Aldehydes / Ketones; Amines / Ammonium Compounds; Green Chemistry; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Instrumental Methods; IR Spectroscopy; Laboratory Instruction; NMR Spectroscopy; Organic Chemistry; Oxidation / Reduction; Second-Year Undergraduate; Solids
*  History
 Created:
Last Updated:		 4/24/2006
4/25/2006
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