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Rapid Eco-Friendly Synthesis and Structure of 3-Hydroxy-3-nitromethyl-1,3-dihydro-indol-2-one

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Abstract

3-Hydroxy-3-nitromethyl-1,3-dihydro-indol-2-one was synthesized from isatin by Henry reaction using an eco-friendly method and characterized by NMR and MS. The crystal structure was determined from single-crystal X-ray diffraction data. It crystallizes in the orthorhombic space group, Pbca, with unit cell dimensions a = 10.515 (2) Å, b = 7.3736 (14) Å, and c = 23.261 (4) Å. The two rings are coplanar and the angle between hydroxyl group and nitromethyl group is 109.07(9)°. In the crystal structure, intermolecular N–H···O and O–H···O hydrogen bonds are responsible for the formation of a 3-dimensional network. No intramolecular hydrogen bond exists.

Graphical Abstract

3-Hydroxy-3-nitromethyl-1,3-dihydro-indol-2-one was synthesized from isatin by Henry reaction using an eco-friendly method and characterized by NMR and MS. The crystal structure was determined from single-crystal X-ray diffraction data. Intermolecular N–H···O and O–H···O hydrogen bonds are responsible for the formation of a 3-dimensional network. No intramolecular hydrogen bond exists.

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Acknowledgments

This work was financially supported by the grants from Scientific Research Plan Projects of Natural Science Research Plan Projects of Shaanxi Science and Technology Department (SJ08B20), Scientific Research Plan Projects of Shaanxi Education Department (08JK413, 09JK702) and Scientific Research Foundation for PhD of Xi’an Shiyou University (Z08008).

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Authors and Affiliations

  1. College of Chemistry & Chemical Engineering, Xi’an Shiyou University, Xi’an, Shaanxi, 710065, People’s Republic of China

    Gang Chen, Ying Tang, Qun-Zheng Zhang & Ya Wu

  2. Key Laboratory of Chemistry for Natural Products of Guizhou Province and Chinese Academy of Sciences, Guizhou, Guiyang, 550002, People’s Republic of China

    Shun-Zhen Mu

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  1. Gang Chen
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  2. Ying Tang
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  3. Qun-Zheng Zhang
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  4. Ya Wu
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Correspondence to Gang Chen.

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Chen, G., Tang, Y., Zhang, QZ. et al. Rapid Eco-Friendly Synthesis and Structure of 3-Hydroxy-3-nitromethyl-1,3-dihydro-indol-2-one. J Chem Crystallogr 40, 369–372 (2010). https://doi.org/10.1007/s10870-009-9662-5

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  • DOI: https://doi.org/10.1007/s10870-009-9662-5

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