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

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

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676-58-4 Synthesis

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1129-30-2
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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