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Eco-Friendly and Highly Efficient Multigram Synthesis of N-(2- Hydroxyethyl)-2-Oxo-2H-Chromene-3-Carboxamide as a Useful Intermediate Using Sonochemistry

[ Vol. 5 , Issue. 2 ]

Author(s):

Ligia S. da Silveira Pinto and Marcus V. N. de Souza*   Pages 104 - 107 ( 4 )

Abstract:


This study describes a new, simple and efficient process for the preparation of N-(2- hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide, on a multigram scale (0.38 moles), by using ultrasound irradiation as green chemistry method. Optimal conditions and yield (83%) were obtained by using 1.2 molar equivalents of ethanolamine at 675 W for 5.0 hours. This intermediate is very versatile and could be transformed in a wide range of derivatives, which could be employed in different areas, such as inorganic complexes, dyes, pesticides and fluorescent coumarins. In the medicinal chemistry, N-(2-hydroxyethyl)-2-oxo-2H-chromene-3-carboxamide is also very useful because a wide variety of compounds could be synthesized and evaluated with diverse types of diseases. In this context, it can be mentioned N-(2-chloroethyl)-2-oxo-2H-chromene-3-carboxamide, a useful intermediate, which was synthesized in this work in gram scale (0.04 moles) in 80% of yield, that could react with diverse types of nucleophiles.

Keywords:

Green chemistry, sonochemistry, ultrasound, multigram, coumarin, intermediate.

Affiliation:

Departamento de Quimica Organica, Instituto de Quimica, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Instituto de Tecnologia em Farmacos-Far-Manguinhos, FioCruz-Fundacao Oswaldo Cruz, Rio de Janeiro

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