5-Nitrofurfural → N-(3-Hydroxymethylphenyl)-alpha-(5-nitro-2-furyl)nitrone

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Reaction Steps

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 5-nitro-2-furaldehyde (65) (1.41 g, 10 mmol) afforded, after workup, a yellow solid. The crude product was recrystallized from acetone/petroleum ether to obtain 1.85 g (7.06 mmol, 71%) of 96 as a yellow crystalline solid: mp 187°-188° C.; IR (CH2Cl2) 3310, 1550, 1520, 1340, 1140, 1025, 1002, 802 cm-1 ; 1H NMR (Me2SO-d6) δ 4.5 (d, J=5.6 Hz, 2H), 5.39 (t, J=5.6, 1H), 7.48-7.93 (m, 6H), 9.01 (s, 1H); 13C NMR (Me2SO-d6) δ 62.81, 115.39, 117.26, 119.49, 119.74, 123.41, 123.56, 129.22, 129.53, 144.88, 147.17, 150.15, 151.78. Anal. Calcd for C12H10N2O5 : C, 54.96; H, 3.81. Found: C, 55.35; H, 3.88.

Provenance & Evidence