Regioselectively [15NO2]-labeled N-methoxypicramide and DPPH prepared by using crown ether and solid sodium [15N]nitrite |
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| Authors: | M T Caproiu I C Covaci P Ionita C Luca T Constantinescu A T Balaban |
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| Institution: | (1) NMR Department, Institute of Organic Chemistry, Spl. Independentei 202 B, PO Box 258, Bucharest 15, Romania;(2) Institute of Physical Chemistry, Spl. Independentei 202, 77208 Bucharest, Romania;(3) Department of Analytical Chemistry, Polytechnic University Bucharest, Spl. Independentei 313, 77207 Bucharest, Romania;(4) Department of Organic Chemistry, Polytechnic University Bucharest, Spl. Independentei 313, 77207 Bucharest, Romania |
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| Abstract: | The present paper reports the regioselective 15NO2]-labeling of N-methoxy-2,4,6-trinitroaniline and 2,2-diphenyl-1-picrylhydrazine (reduced DPPH). Starting from N-methoxy-2,6-dinitroaniline,
or N-methoxy-2,4-dinitroaniline, nitration in methylene chloride with solid sodium 15N]nitrite and 15-crown-5-ether afforded N-methoxy-2,6-dinitro-4-15N]nitroaniline and N-methoxy-2,4-dinitro-615N]nitroaniline, respectively. The same compounds could be prepared in higher purity by nitrodecarboxylation (ipso-substitution) under the same conditions starting from N-methoxy-4-carboxy-2,6-dinitroaniline (4-methoxyamino-3,5-dinitrobenzoic
acid) and N-methoxy-2-carboxy-4,6-dinitroaniline (2-methoxyamino-3,5-dinitrobenzoic acid). Similarly,ipso-substitution of 2,2-diphenyl-1-(4-carboxy-2,6-dinitrophenyl)-hydrazine afforded, under the same reaction conditions, 2,2-diphenyl-1-(2,6-dinitro-4-15N]nitrophenyl)-hydrazine. By1H-NMR and13C-NMR it was also observed that under these reaction conditions a14NO2 group can be replaced by a15NO2 group. |
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