Hydrogen Peroxide → 5-(Hydroxymethyl)pyridine-2-carboxylic acid

HRID 370436Notes

Reaction equation

HRID 370436 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][N:4]=1)=[O:2].[OH:11]O>O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][N:4]=1)([OH:11])=[O:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 135185625-(Hydroxymethyl)pyridine-2-carboxaldehyde

Product 1

HCID 135185635-(Hydroxymethyl)pyridine-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Formyl-5-hydroxymethylpyridine (5.7 g, 0.042 mol) was dissolved in 40 mL of H2O and treated with 10 mL of aqueous 30% H2O2 at room temperature for 16 h. The mixture was concentrated to about 20 mL and cooled, and the precipitated acid was collected by filtration. 2-Carboxy-5-hydroxymethylpyridine was obtained in 97% yield (6.1 g). A portion was recrystallized from H2O to obtain an analytical sample. These white crystals sublimed at about 220° C., IR (mull) 3200, 1670, 1600, 1380, 1070, 870, 850, 800 cm-1 ; 1H NMR (Me2SO-d6) δ4.73 (s, 2, CH2OH), 7.9-8.2 (m, 2, 3', 4'--H), 8.67 (m, 1, 6'--H); MS calcd for C7H7NO3 153.0426, found 153.0429.

Workup

  1. concentrationThe mixture was concentrated to about 20 mL
  2. temperaturecooled
  3. filtrationthe precipitated acid was collected by filtration

Sources & evidence

ORD record
ord-614e27f878a04e57b730fee4b949881d
Source dataset
uspto-grants-1985_07
Patent number
US04526787

Reaction notes

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