Water → 3-Methylsulfonamido-2-pyridinecarboxaldehyde

HRID 7155

Reaction equation

HRID 7155 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[C:7]([CH3:12])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].O.[Se](=O)=[O:15]>O1CCOCC1>[CH3:1][S:2]([NH:5][C:6]1[C:7]([CH:12]=[O:15])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 220186853-Methylsulfonamido-2-methylpyridine

Product 1

HCID 220186543-Methylsulfonamido-2-pyridinecarboxaldehydeYield 83.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-methylsulfonamido-2-methylpyridine (310 mg, 1.66 mmol) in dioxane (8 mL) was added water (0.8 mL) and selenium(IV) oxide (241 mg, 2.17 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ethyl acetate, 1:1) to afford the title compound (278 mg, 83%). 1H NMR (CDCl3) □ 3.14 (s, 3H), 7.53 (dd, 1H, J=9, 6 Hz), 8.16 (dd, 1H, J=9, 3 Hz), 8.53 (dd, 1H, J=6, 3 Hz), 10.09 (s, 1H), 10.41 (br s, 1H, NH).

Workup

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-1781f000e508492c963f107d63b76858
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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