Chemistry:2-Aminoacetanilide
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| Names | |
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| Preferred IUPAC name
N-(2-Aminophenyl)acetamide | |
| Other names
o-Aminoacetanilide, N-2-Aminophenylacetamide, 2′-Acetamidoaniline
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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| UNII | |
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| Properties | |
| C8H10N2O | |
| Molar mass | 150.18 g/mol |
| Appearance | Solid |
| Density | 1.1392 |
| Melting point | 133-137 |
| Boiling point | 271.72 |
| Hazards | |
| GHS pictograms | 
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| GHS Signal word | Warning |
| H315, H319, H335 | |
| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
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,[1][2][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]
References
- ↑ 1.0 1.1 Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (7 June 2016). "A review on Synthesis of Aminoacetanilides". Integrated Research Advances 3: 30–39. ISSN 2456-334X. http://pubs.iscience.in/journal/index.php/ira/article/view/471.
- ↑ 2.0 2.1 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"] (in en). Tetrahedron 57 (9): 1793–1799. doi:10.1016/S0040-4020(00)01158-3. https://linkinghub.elsevier.com/retrieve/pii/S0040402000011583.
- ↑ 3.0 3.1 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" (in en). Green Chem. 15 (1): 95–99. doi:10.1039/C2GC36517K. ISSN 1463-9262. http://xlink.rsc.org/?DOI=C2GC36517K.
- ↑ 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" (in en). Journal of Medicinal Chemistry 52 (20): 6447–6455. doi:10.1021/jm9009873. ISSN 0022-2623. PMID 19785436.
- ↑ Faustino, H.; Brannigan, C.R.; Reis, L.V.; Santos, P.F.; Almeida, P. (October 2009). "Novel azobenzothiazole dyes from 2-nitrosobenzothiazoles" (in en). Dyes and Pigments 83 (1): 88–94. doi:10.1016/j.dyepig.2009.03.018. https://linkinghub.elsevier.com/retrieve/pii/S0143720809000680.
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