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

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Reaction Steps

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 3-nitrobenzaldehyde (57) (1.51 g, 10 mmol) afforded, after workup, a light yellow solid. The crude product was recrystallized from acetone/petroleum ether to obtain 1.90 g (6.98 mmol, 70%) of 92 as a pale yellow crystalline solid: mp 177°-179° C.; IR (Nujol) 3220, 1570, 1530, 1350, 1040, 800 cm-1 ; 1H NMR (Me2SO-d6) δ 4.58 (d, J=5.6 Hz, 2H), 5.39 (t, J=4.8, 2H), 7.45-9.53 (m, 9H); 13C NMR (Me2SO-d6) δ 62.91, 119.87, 120.25, 122.98, 125.19, 128.68, 129.42, 130.47, 132.40, 132.94, 135.30, 144.73, 148.26, 148.73. Anal. Calcd for C14H12N2O4 : C, 61.76; H, 4.41. Found: C, 61.99; H, 4.52.

Provenance & Evidence