Crystal structure of 3-(4-azidophenyl)pentane-2,4-dione, C11H11N3O2

Michael Hummel, Egon Rubatscher, Klaus Wurst, Gerhard Laus, Peter Jaitner, Herwig Schottenberger
2009 Zeitschrift für Kristallographie - New Crystal Structures  
C 11H11N3O2,t riclinic, P1 (no. 2), a =7.4695(7) Å, b =10.6088(6) Å, c =14.0710(9) Å, a =92.586 (5) Source of material The title compound was prepared from 3-(4-nitrophenyl)pentane-2,4-dione [1] by reduction, diazotization and substitution. The synthesis of the nitro and amino compounds has been described earlier [2], but it was not reproducible. Therefore, the synthesis of the nitro compound was conducted in analogy to an improved procedure [3] . Also, an improved reduction to the amino
more » ... to the amino compound using SnCl 2 was employed in analogy to apublished procedure [4] . In the next step, the respective diazonium hexafluorophosphate was prepared using aqueous sodium nitrite in the presence of hexafluorophosphoric acid. Finally, aqueous sodium azide was applied for the conversion to the desired product. The overall yield of this four-step process was 12 %. Suitable crystals were obtained from diethyl ether. IR and NMR spectra are available in the CIF. Experimental details The hydrogen atoms at O1 or O2 and O3 or O4 of the acetylacetonyl groups were calculated in the form of a1:1disorder model with occupancy of 0.5 for each hydrogen position. The hydrogen atoms were allowed to rotate about the C-Ob onds. Furthermore, the crystal structure was analyzed for additional symmetry, but none was found.
doi:10.1524/ncrs.2009.0293 fatcat:mnj4db7z35gixnvejx4uquuosq