2-Aminoacetanilide

2-aminoacetanilide
Names
	Preferred IUPAC name N-(2-Aminophenyl)acetamide
	Other names o-Aminoacetanilide, N-2-Aminophenylacetamide, 2′-Acetamidoaniline
	Identifiers
CAS Number	34801-09-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	10676;
ECHA InfoCard	100.156.006
PubChem CID	11149;
UNII	LB34XRQ95V;
CompTox Dashboard (EPA)	DTXSID4043854 ;
	InChI InChI=1S/C8H10N2O/c1-6(11)10-8-5-3-2-4-7(8)9/h2-5H,9H2,1H3,(H,10,11) Key: MPXAYYWSDIKNTP-UHFFFAOYSA-N;
	SMILES CC(=O)NC1=CC=CC=C1N;
	Properties
Chemical formula	C8H10N2O
Molar mass	150.18 g/mol
Appearance	Solid
Density	1.1392
Melting point	133-137
Boiling point	271.72
	Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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

^ ^a ^b Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (7 June 2016). "A review on Synthesis of Aminoacetanilides". Integrated Research Advances. 3: 30–39. ISSN 2456-334X – via Google Scholar.
^ ^a ^b 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. 57 (9): 1793–1799. doi:10.1016/S0040-4020(00)01158-3.
^ ^a ^b 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. 15 (1): 95–99. doi:10.1039/C2GC36517K. ISSN 1463-9262.
^ 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. 52 (20): 6447–6455. doi:10.1021/jm9009873. ISSN 0022-2623. PMC 3319430. PMID 19785436.
^ Faustino, H.; Brannigan, C.R.; Reis, L.V.; Santos, P.F.; Almeida, P. (October 2009). "Novel azobenzothiazole dyes from 2-nitrosobenzothiazoles". Dyes and Pigments. 83 (1): 88–94. doi:10.1016/j.dyepig.2009.03.018.

[:0-1] Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (7 June 2016). "A review on Synthesis of Aminoacetanilides". Integrated Research Advances. 3: 30–39. ISSN 2456-334X – via Google Scholar.

[:1-2] 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. 57 (9): 1793–1799. doi:10.1016/S0040-4020(00)01158-3.

[xlink.rsc.org-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. 15 (1): 95–99. doi:10.1039/C2GC36517K. ISSN 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. 52 (20): 6447–6455. doi:10.1021/jm9009873. ISSN 0022-2623. PMC 3319430. PMID 19785436.

[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. 83 (1): 88–94. doi:10.1016/j.dyepig.2009.03.018.

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