Paper
Synthesis and Crystal Structures of 4-(3-Nitropyridin-2-ylamino)phenol and 4-(3-Aminopyridin-2-ylamino)phenol
Published May 12, 2011 · Sheng-li Cao, Jie Zhao, Nan Zhang
Journal of Chemical Crystallography
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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) Å, b = 8.7389(17) Å, c = 10.684(3) Å 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) Å, b = 14.2181(18) Å, c = 7.9836(15) Å 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.Graphical AbstractThe preparation and crystal structures of 4-(3-nitropyridin-2-ylamino)phenol and 4-(3-aminopyridin-2-ylamino)phenol are reported.
The crystal structures of 4-(3-nitropyridin-2-ylamino)phenol and 4-(3-aminopyridin-2-ylamino)phenol show their potential as intermediates in the synthesis of potential antitumor agent ABT-751.
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