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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 32, 2002 - Issue 3
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Original Articles

A SOLVENT-FREE AND FORMALIN-FREE ESCHWEILER-CLARKE METHYLATION FOR AMINES

, , , , &
Pages 457-466 | Received 19 Mar 2001, Published online: 16 Aug 2006
 

ABSTRACT

Primary and secondary amines are N-methylated by a mixture of paraformaldehyde and oxalic acid dihydrate in good to excellent yields. The reaction proceeds without involvement of organic solvents and toxic formalin. Reaction temperatures of 100°C are required for the decomposition of oxalic acid into the intermediate formic acid which acts as the actual reductant. The reaction conditions have been optimized, and the mechanism has been elucidated by means of deuteration experiments.

ACKNOWLEDGMENT

The authors are grateful to the Christian-Doppler-Forschungsgesellschaft, Vienna, Austria, and to Lenzing AG, Lenzing, Austria, for financial support.

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