5-Hydroxy-2-hydroxymethylpyridine → 5-Hydroxy-2-pyridinecarboxaldehyde

HRID 1964791Notes

Reaction equation

HRID 1964791 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1>C(O)(C)C.CC(C)=O.C(#N)C.O=[Mn]=O>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1

Participants

5

Reactant 1

HCID 4194905-Hydroxy-2-hydroxymethylpyridine

Product 1

HCID 2783895-Hydroxy-2-pyridinecarboxaldehydeYield 21.8%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalystHCID 3776IsopropanolSolventHCID 21918305Acetone acetonitrileSolvent

Procedure

A mixture of 5-hydroxy-2-hydroxymethylpyridine (14 g) and MnO2 (100 g) in isopropylalcohol (600 mL) was stirred under N2 for 20 h. The reaction mixture was filtered and filtrate concentrated under vacuum affording a crude product as a solid (12 g). It was suspended in acetone/acetonitrile (25 mL each) and the solid residue was filtered off. It was washed with cold acetone/acetonitrile 1:1 mixture to give pure 5-hydroxypyridine-2-carboxaldehyde (3 g) as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationfiltrate concentrated under vacuum
  3. customaffording a crude product as a solid (12 g)
  4. filtrationthe solid residue was filtered off
  5. washIt was washed with cold acetone/acetonitrile 1:1 mixture

Sources & evidence

ORD record
ord-1824433beca145a081f4b22da3b42a41
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

Loading…