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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 4
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Original Articles

A Convenient One Pot Procedure for N-Methylation of Aromatic Amines Using Trimethyl Orthoformate

Seetharamaiyer Padmanabhan Cambridge NeuroScience Inc., One Kendall Square, Building #700, Cambridge, MA, 02139, U.S.A.
,
N. Laxma Reddy Cambridge NeuroScience Inc., One Kendall Square, Building #700, Cambridge, MA, 02139, U.S.A.
&
Graham J. Durant Cambridge NeuroScience Inc., One Kendall Square, Building #700, Cambridge, MA, 02139, U.S.A.
Pages 691-699 | Received 16 Aug 1996, Published online: 20 Aug 2006
 
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Abstract

Aromatic amines react with trimethyl orthoformate in the presence of concentrated sulfuric acid followed by acid hydrolysis to afford mono methylated amines in moderate to good yields.

Notes

The final guanidine derivatives derived from the N-methylaniline derivatives (7a & 7b) gave satisfactory microanalyses, 1H-NMR, MS data and HPLC purity.

HPLC purity estimation was not carried out.

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