Title:Eco-Friendly and Highly Efficient Multigram Synthesis of N-(2- Hydroxyethyl)-2-Oxo-2H-Chromene-3-Carboxamide as a Useful Intermediate Using Sonochemistry
VOLUME: 5 ISSUE: 2
Author(s):Ligia S. da Silveira Pinto and Marcus V. N. de Souza*
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
Keywords:Green chemistry, sonochemistry, ultrasound, multigram, coumarin, intermediate.
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.
