Synthesis and Crystal Structures of 4-(3-Nitropyridin-2-ylamino)phenol and 4-(3-Aminopyridin-2-ylamino)phenol |
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Authors: | Sheng-Li Cao Jie Zhao Nan Zhang Yue Wang Yu-Yang Jiang Yu-Ping Feng |
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Institution: | (1) Department of Chemistry, Capital Normal University, Beijing, 100048, People’s Republic of China;(2) Key Laboratory of Chemical Biology, Guangdong Province, Graduate School at Shenzhen, Tsinghua University, Shenzhen, 518055, People’s Republic of China;(3) Key Laboratory of Bioorganic Phosphorus Chemistry and Chemical Biology, Department of Chemistry, Ministry of Education, Tsinghua University, Beijing, 100084, People’s Republic of China |
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Abstract: | Abstract The title compounds, 4-(3-nitropyridin-2-ylamino)phenol (I) and 4-(3-aminopyridin-2-ylamino)phenol (II), are two intermediates for the synthesis of a potential antitumor agent ABT-751. The reaction of 4-aminophenol with 2-chloro-3-nitropyridine
yielded I which was converted into II by reduction. Instead of the Pd/C catalytic hydrogenation described in many literature, reduction with cheap sodium sulfide
in aqueous media was utilized for shorting the reaction time and simplifying the operation. The crystal structures of the
resultant compounds were determined by single-crystal X-ray diffraction. The compound I is crystallized in P21/c space group of monoclinic system, with a = 11.5236(19) ?, b = 8.7389(17) ?, c = 10.684(3) ? and α = 90.00°, β = 107.76(3)°, γ = 90.00°. The compound II is crystallized in Cc space group of monoclinic system, with a = 10.688(2) ?, b = 14.2181(18) ?, c = 7.9836(15) ? and α = 90.00°, β = 125.801(7)°, γ = 90.00°. In both crystal structures, the intermolecular N–H–O and O–H–N
hydrogen bonds link the molecules, which effectively stabilize the structures. |
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