2-Pyridinecarboxaldehyde → N-(3-Hydroxymethylphenyl)-alpha-(2-pyridyl)nitrone

HRID 845592Notes

Reaction equation

HRID 845592 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]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]=O>>[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([N+:9]([O-:10])=[CH:17][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 142732-PyridinecarboxaldehydeHCID 20131568N-(3-Hydroxymethylphenyl)hydroxylamine

Product 1

HCID 86742279N-(3-Hydroxymethylphenyl)-alpha-(2-pyridyl)nitroneYield 65%

Procedure

The reaction of hydroxylamine 91 (1.36 g, 10 mmol) with 2-pyridinecarboxaldehyde (63) (1.07 g, 10 mmol) afforded, after workup, a yellow oil. The crude product was purified by passing through a short column of silica gel with 20:1 ethyl acetate/methanol as the eluant then recrystallized from acetone/petroleum ether to obtain 1.48 g (6.5 mmol, 65%) of 95 as a yellow crystalline solid: mp 117°-119° C.; IR (CH2Cl2) 3610, 3340, 1580, 1550, 1390, 1090 cm-1 ; 1H NMR (CDCl3) δ 4.53 (t, J=5.8, 1H), 4.65 (d, J=5.6 Hz, 2H), 7.28-9.27 (m, 9H); 13C NMR (CDCl3) δ 63.86, 119.70, 120.37, 124.33, 124.91, 128.59, 129.31, 135.80, 137.25, 143.61, 148.62, 149.50, 149.84. Anal. Calcd for C13H12N2O2 : C, 68.42; H, 5.26. Found: C, 68.52; H, 5.30.

Workup

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

Sources & evidence

ORD record
ord-8b56cc09696f471e8f93a0f082a73098
Source dataset
uspto-grants-1988_07
Patent number
US04758669

Reaction notes

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