4-Nitrobenzaldehyde → N-(3-Hydroxymethylphenyl)-alpha-(4-nitrophenyl)nitrone

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Reaction Steps

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 4-nitrobenzaldehyde (58) (1.51 g, 10 mmol) afforded, after workup, a red solid. The crude product was recrystallized from acetone/petroleum ether to obtain 2.21 g (8.1 mmol, 81%) of 93 as a red crystalline solid: mp 207°-209° C.; IR (Nujol) 3260, 1590, 1555, 1510, 1320, 1150, 1020, 860 cm-1 ; 1H NMR (Me2SO-d6) δ 4.60 (d, J=5.6 Hz, 2H), 5.43 (t, J=5.7 Hz, 1H), 7.49-8.71 (m, 9H); 13C NMR (Me2SO-d6) δ 62.85, 119.99, 120.38, 124.29, 128.83, 129.47, 129.96, 132.70, 137.36, 144.79, 147.83, 148.94. Anal. Calcd for C14H12N2O4 : C, 61.76; H, 4.41. Found: C, 62.09; H, 4.59.

Provenance & Evidence