2-Nitrobenzaldehyde → N-(3-Hydroxymethylphenyl)-alpha-(2-nitrophenyl)nitrone

Participants

Reaction Steps

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 2-nitrobenzaldehyde (59) (1.51 g, 10 mmol) afforded, after workup, a yellow oil. The crude product was recrystallized from acetone/petroleum ether to obtain 1.74 g (6.4 mmol, 64%) of 94 as a yellow crystalline solid: mp 97°-99° C.; IR (CH2Cl2) 3605, 1570, 1525, 1340, 1155 cm-1 ; 1H NMR (Me2SO-d6) δ 4.60 (d, J=5.6 Hz, 2H), 5.43 (t, J=5.6 Hz, 1H), 7.49-8.74 (m, 9H); 13C NMR (Me2SO-d6) δ 62.82, 119.85, 120.24, 124.84, 125.06, 128.85, 129.54, 129.79, 130.84, 131.28, 133.83, 144.86, 148.44, 148.55. Anal. Calcd for C14H12N2O4 : C, 61.76; H, 4.41. Found: C, 61.85; H, 4.58.

Provenance & Evidence