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

HRID 845594Notes

Reaction equation

HRID 845594 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:20])=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1>CS(C)=O.[Mn]>[CH:2]([C:3]1[CH:4]=[C:5]([N+:9]([O-:20])=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1)=[O:1]

Participants

4

Reactant 1

HCID 86742276N-(3-Hydroxymethylphenyl)-alpha-(3-nitrophenyl)nitrone

Product 1

HCID 86742281N-(3-Formylphenyl)-alpha-(3-nitrophenyl)nitroneYield 69%

Reagents, catalysts & solvents 2

HCID 23930ManganeseCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-(3-hydroxymethylphenyl)-α-(3-nitrophenyl)nitrone (92) (1.38 g, 5.1 mmol) in dimethyl sulfoxide (50 mL) was added active manganese dioxide82 (15 g). The resulting mixture was stirred at room temperature for 21/2 h. The mixture was filtered and the solvent was slowly poured into water (200 mL), and the precipitate product was collected. The crude product was dissolved in dichloromethane, and the solution was washed with water (50 mL). The solution was then dried (MgSO4), and the solvent was removed with a rotary evaporator. Recrystallization from dichloromethane/petroleum ether afforded 0.95 g (3.5 mmol, 69%) of 89 as a yellow crystalline solid: mp 195°-197° C.; IR (Nujol) 1690, 1525, 1340, 1150, 1060, 790 cm-1 ; 1H NMR (Me2SO-d6) δ 7.77-8.74 (m, 7H), 8.93 (s, 1H), 9.53 (s, 1H), 10.10 (s, 1H); 13C NMR (Me2SO-d6) δ 122.44, 123.26, 125.58, 127.64, 130.67, 130.85, 131.76, 132.73, 133.15, 135.48, 137.54, 148.34, 149.15, 192.78; mass spectrum, m/e (relative intensity) 270 (M+, 13.1), 254 (19.8), 119 (100), 91 (72.6), 77 (146.4); high resolution mass spectrum, m/e 270.0644 (calcd for C14H10N2O4, 270.0640).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe solvent was slowly poured into water (200 mL)
  3. customthe precipitate product was collected
  4. dissolutionThe crude product was dissolved in dichloromethane
  5. washthe solution was washed with water (50 mL)
  6. dry with materialThe solution was then dried (MgSO4)
  7. customthe solvent was removed with a rotary evaporator
  8. customRecrystallization from dichloromethane/petroleum ether

Sources & evidence

ORD record
ord-38abce2226274504909f78a837c2e8dc
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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