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

HRID 845591Notes

Reaction equation

HRID 845591 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:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O)([O-:13])=[O:12]>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:10])=[CH:16][C:15]2[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=2[N+:11]([O-:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 111012-NitrobenzaldehydeHCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Product 1

HCID 86742278N-(3-Hydroxymethylphenyl)-alpha-(2-nitrophenyl)nitroneYield 64%

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-08893c524c75402c81c88ee89f956bfd
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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