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

HRID 845593Notes

Reaction equation

HRID 845593 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][OH:10])[CH:6]=[CH:7][CH:8]=1.[N+:11]([C:14]1[O:18][C:17]([CH:19]=O)=[CH:16][CH:15]=1)([O-:13])=[O:12]>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:10])=[CH:19][C:17]2[O:18][C:14]([N+:11]([O-:13])=[O:12])=[CH:15][CH:16]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 127745-NitrofurfuralHCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Product 1

HCID 86742280N-(3-Hydroxymethylphenyl)-alpha-(5-nitro-2-furyl)nitroneYield 71%

Procedure

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.

Workup

  1. customafforded
  2. customThe crude product was recrystallized from acetone/petroleum ether

Sources & evidence

ORD record
ord-9e6a4a0a2dcd45cf87c4c112f9e4d320
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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