2-Aminoacetanilide Explained

2-Aminoacetanilide is a chemical compound which is a amino derivative of acetanilide and ortho-isomer of aminoacetanilide. There are two other isomers of aminoacetanilide, 3-aminoacetanilide and 4-aminoacetanilide. Aminoacetanilide derivatives are important synthetic intermediates in heterocyclic and aromatic synthesis. These derivatives have found applications in pharmaceutical industry and dyes and pigment industry.^[1]

Synthesis

Catalytic hydrogenation of 2-nitroacetanilide using 10%Pd/C gives 2-aminoacetanilide.^[2]

Uses

2′-Aminoacetanilide is starting material for the synthesis of 2-methylbenzimidazole,^[3] N-(2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-''d'']pyrimidin-6(2H)-yl)phenyl)-5-methylfuran-2-carboxamide,^[4] and azobenzothiazole dyes, N-[2-(6-nitrobenzothiazol-2-ylazo)phenyl]acetamide and N-[2-(benzothiazol-2-ylazo)phenyl]acetamide.^[5] Benzimidazoles have been synthesized by cyclization of 2′-aminoacetanilide by CO₂ in the presence of H₂ using RuCl₂(dppe)₂ as the catalyst.^[3]

Notes and References

1. Singh. Raman. Kau. Rajneesh. Singh. Kuldeep. 7 June 2016. A review on Synthesis of Aminoacetanilides. Integrated Research Advances. 3. 30–39. 2456-334X. Google Scholar.
2. Fonseca. Tatiana. Gigante. Bárbara. Gilchrist. Thomas L. February 2001. A short synthesis of phenanthro[2,3- d ]imidazoles from dehydroabietic acid. Application of the methodology as a convenient route to benzimidazoles]. Tetrahedron. en. 57. 9. 1793–1799. 10.1016/S0040-4020(00)01158-3.
3. Yu. Bo. Zhang. Hongye. Zhao. Yanfei. Chen. Sha. Xu. Jilei. Huang. Changliang. Liu. Zhimin. 2013. Cyclization of o-phenylenediamines by CO 2 in the presence of H 2 for the synthesis of benzimidazoles. Green Chem.. en. 15. 1. 95–99. 10.1039/C2GC36517K. 1463-9262.
4. Tradtrantip. Lukmanee. Sonawane. N. D.. Namkung. Wan. Verkman. A. S.. 2009-10-22. Nanomolar Potency Pyrimido-pyrrolo-quinoxalinedione CFTR Inhibitor Reduces Cyst Size in a Polycystic Kidney Disease Model. Journal of Medicinal Chemistry. en. 52. 20. 6447–6455. 10.1021/jm9009873. 19785436. 3319430. 0022-2623.
5. Faustino. H.. Brannigan. C.R.. Reis. L.V.. Santos. P.F.. Almeida. P.. October 2009. Novel azobenzothiazole dyes from 2-nitrosobenzothiazoles. Dyes and Pigments. en. 83. 1. 88–94. 10.1016/j.dyepig.2009.03.018.