(Z)-3-[(2-Methoxyphenyl)carbamoyl]propenoic acid synthesis

Yield:31460-26-1 99%

Reaction Conditions:

in dichloromethane; for 49 h;Heating;

Steps:

4.2.3. General procedure to synthesize aryl maleamic acids(11a-i)

General procedure: Maleic anhydride (0.004 mol) and the appropriate aryl amine(0.004 mol) were dissolved in dichloromethane (100 mL) and werestirred for a time period that ranged between 30 min and 48 hdepending on the aryl amine used. Heat was also applied for certainaryl amides to speed up the reaction. TLC plates were usedto monitor the progress of the reactions (5% methanol/dichloromethane).The solvents were removed by vacuum, the precipitateswere then washed with dichloromethane, filtered under suctionand dried. The aryl maleamic acids were obtained as powdersand were very pure as was evident by their melting points andtheir NMR spectra.Deviations from procedure: Compounds 11d and 11f had to bestirred for 48 h and heat had to be applied for one hour. The reactionsstill did not go all the way to completion so the solvents wereremoved by suction filtration rather than vacuum. Compound 11ihad to be stirred for 12 h, compounds 11g and 11h needed stirringfor 4 h and reactions leading to compounds 11a, 11b, 11c and 11ewere complete within 30 min.

References:

Jha, Amitabh;Duffield, Katherine M.;Ness, Matthew R.;Ravoori, Sujatha;Andrews, Gabrielle;Bhullar, Khushwant S.;Rupasinghe, H.P. Vasantha;Balzarini, Jan [Bioorganic and Medicinal Chemistry,2015,vol. 23,# 19,art. no. 12527,p. 6404 - 6417]