ChemicalBook CAS DataBase List 2,6-Diacetylpyridine

2,6-Diacetylpyridine synthesis

9synthesis methods

Product Name:2,6-Diacetylpyridine
CAS Number:1129-30-2
Molecular formula:C9H9NO2
Molecular Weight:163.17

935-28-4

1129-30-2

The general procedure for the synthesis of 2,6-diacetylpyridine from 2,6-diethylpyridine was as follows: 1.0 equiv. of N-hydroxyphthalimide (NHPI) was added to a 25 mL Schlenk reaction tube and dried under vacuum for 15 min. Subsequently, acetonitrile was added as a solvent under oxygen atmosphere, followed by 2.0 equivalents of tert-butyl nitrite and 0.5 mmol of 2,6-diethylpyridine. After sealing the reaction tube with a polytetrafluoroethylene plug, it was immersed in an oil bath preheated to 90°C for 36 hours. After completion of the reaction, the solvent acetonitrile was removed by distillation under reduced pressure. The crude product was purified by column chromatography with the eluent being petroleum ether/ethyl acetate (5:1, v/v) to give 2,6-diacetylpyridine. The product was a yellow solid in 54% yield.

2,6-Pyridinedicarboxamide, N2,N2,N6,N6-tetraethyl-

36763-33-4
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676-58-4 Synthesis

676-58-4
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$15.00/25ml

1129-30-2
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$6.00/250mg

Yield:1129-30-2 88%

Reaction Conditions:

Stage #1: N²,N²,N⁶,N⁶-tetraethyl-2,6-pyridinedicarboxamide;methylmagnesium chloride in tetrahydrofuran at 0 - 20; for 3 h;
Stage #2: with hydrogenchloride in tetrahydrofuran;water at 0;

Steps:

2,6-Diacetylpyridine (2)

A solution of MeMgCl in THF (~20%) (9 mL, 19 mmol) was added dropwise at 0° C to a solution of 2,6-bis(1-pyrrolidinylcarbonyl)pyridine (2.0 g, 7.3 mmol) in anhydrous THF (15 mL). After 3 hours of stirring at room temperature, 30 mL of 2M aq. HCl was added at 0° C and stirred until the evaluation of the gas ceased. The mixture was extracted with СH2Cl2 (3×20 mL). Combined organic phase was dried over Na2SO4. After removal of the solvent in vacuo the product was recrystallized from hexane to yield colorless powder 1.05 g (88%).

References:

Ivchenko, Pavel V.;Nifant'Ev, Ilya E.;Buslov, Ivan V. [Tetrahedron Letters,2013,vol. 54,# 3,p. 217 - 219] Location in patent:supporting information

935-28-4 Synthesis

935-28-4
72 suppliers
$19.00/100mg

1129-30-2
350 suppliers
$6.00/250mg

References