Synthesis, characterization and crystal structure of methyl 2-(2-oxo-2 H-chromen-4-yl-amino)-benzoate

Henrique V P Hollauer; Rachel C Vilas Novas; Guilherme P Guedes; Camilla D Buarque; Lívia B L Escobar

doi:10.1107/S2056989023007351

Synthesis, characterization and crystal structure of methyl 2-(2-oxo-2 H-chromen-4-yl-amino)-benzoate

Acta Crystallogr E Crystallogr Commun. 2023 Aug 29;79(Pt 9):842-846. doi: 10.1107/S2056989023007351. eCollection 2023 Sep 1.

Authors

Henrique V P Hollauer¹, Rachel C Vilas Novas¹, Guilherme P Guedes², Camilla D Buarque¹, Lívia B L Escobar¹

Affiliations

¹ Chemistry Department, Pontifical Catholic University of Rio de Janeiro, 22451-900 Rio de Janeiro, RJ, Brazil.
² Chemistry Institute, Federal Fluminense Universidade, Niteroi, 24020-141 Rio de Janeiro, Brazil.

Abstract

Methyl 2-(2-oxo-2H-chromen-4-yl-amino)-benzoate, C₁₇H₁₃NO₄ (1), was pre-pared by condensation between 4-hy-droxy-coumarin and methyl 2-amino-benzoate. It crystallizes in the ortho-rhom-bic space group Pca2₁ at 300 K. The mol-ecule of compound 1 consists of the 2H-chromen-2-one part connected by an amine moiety (-NH-) to the methyl benzoate ring. The supra-molecular array is formed by hydrogen bonds between the aromatic ring and the O atoms of the lactone and ester portions. The structural details match the spectroscopic data acquired from NMR and IR spectroscopy.

Keywords: benzoate; coumarin; crystal structure; ester.

Grants and funding

Funding for this research was provided by: Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (grant No. E-26/202.720/2018); Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (grant No. E-26/201.314/2022); Conselho Nacional de Desenvolvimento Científico e Tecnológico (grant No. 304671/2020-7).