Selenium Dioxide → 3-Hydroxy-6-methylpyridine-2-carbaldehyde

HRID 486332

Reaction equation

HRID 486332 reaction equation
[OH:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[Se](=O)=O>O1CCOCC1.C(O)C>[OH:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 1351283-Hydroxy-2-hydroxymethyl-6-methylpyridine

Product 1

HCID 124219863-Hydroxy-6-methylpyridine-2-carbaldehydeYield 57.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Hydroxy-6-methyl-2-pyridine methanol (20.0 g, 0.14 mol) and selenium dioxide(8.0 g, 72 mmol) were dissolved in 140 mL of 1,4-dioxane and 280 mL of absolute ethanol. The resulting mixture was heated at 80°-85° C. for 12 h. The selenium precipitate was removed by filtration and the filtrate was concentrated to dryness in vacuo. The dark red residue was sublimed at 90° C. and 14 mmHg for 6 h to obtain 11.0 g (56%) of pure product, m.p. 101°-102° C.; 1H NMR (CDCl3) δ: 10.50 (br s, 1H), 10.03 (s, 1H), 7.27 (s, 2H); 2.53 (s, 3H).

Workup

  1. temperatureThe resulting mixture was heated at 80°-85° C. for 12 h
  2. customThe selenium precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated to dryness in vacuo
  4. customwas sublimed at 90° C.

Sources & evidence

ORD record
ord-78476dc1c0804450a72973a1fefc0b35
Source dataset
uspto-grants-1994_03
Patent number
US05290942

Linked notes

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