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

HRID 845589Notes

Reaction equation

HRID 845589 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[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([O-:13])=[O:12]>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:10])=[CH:17][C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Product 1

HCID 86742276N-(3-Hydroxymethylphenyl)-alpha-(3-nitrophenyl)nitroneYield 70%

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-0c6dda5c0cdd4d9fa54013a64a93b601
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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