Synlett 2010(19): 2905-2907  
DOI: 10.1055/s-0030-1259029
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Organic Reactions in Water: A Practical and Convenient Method for the N-Formylation of Amines in Water

Babak Kaboudin*, Minoo Khodamorady
Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), Gava Zang, Zanjan 45137-66731, Iran
Fax: +98(241)4249023; e-Mail: [email protected];
Further Information

Publication History

Received 21 June 2010
Publication Date:
10 November 2010 (online)

Abstract

A simple, efficient, scaleable process has been developed for the N-formylation amines in water. Treatment of amines with triethyl orthoformate in water at reflux under neutral conditions without any additives gives the corresponding N-formyl derivatives in good yields.

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20

The amine (3 mmol) and triethyl orthoformate (12 mmol) was added to H2O (8 mL), and the solution was stirred for 3-48 h at reflux or 2-3 h under microwave irradiation at 90 ˚C at ambient pressure in a microwave reactor (a Milestone, Micro SYNTH Microwave Labstation for Synthesis, microwave reactor was used for all experiments). After stirring for the requisite period (Table  [¹] ), the reaction mixture was washed with Et2O (3 × 50 mL). The resulting mixture was subjected to column chromatography on silica gel with EtOAc-n-hexane (2:8) and evaporation of the solvent under reduced pressure to give pure products in
41-87% yields. All products gave satisfactory spectroscopic data according to the literature.¹5