ChemicalBook CAS DataBase List Dimethyl 2,4-pyridinedicarboxylate

Dimethyl 2,4-pyridinedicarboxylate synthesis

6synthesis methods

Product Name:Dimethyl 2,4-pyridinedicarboxylate
CAS Number:25658-36-0
Molecular formula:C9H9NO4
Molecular Weight:195.17

67-56-1

499-80-9

25658-36-0

Phosphorus pentachloride (PCl5, 39 g, 0.186 mol, 3 eq.) and 2,4-pyridinedicarboxylic acid (11.5 g, 6.2 x 10^-2 mol) were added to a 500 mL round bottom flask. The mixture was stirred at room temperature for 45 minutes and the mixture was observed to transform into a green liquid. Subsequently, the reaction mixture was diluted with dichloromethane (80 mL) and methanol (20 mL) was added slowly. The reaction mixture was poured into water (300 mL) containing sodium bicarbonate (NaHCO3, 60 g), the aqueous phase was extracted with dichloromethane (4 x 50 mL) and the combined organic phases were washed with 1 M sodium carbonate (Na2CO3, 2 x 50 mL). The crude product was purified by fast column chromatography (eluent: ethyl acetate/cyclohexane, 75:25). A solid product of 11.71 g was obtained in 96% yield. The product was stored at room temperature.1H NMR (200 MHz, CDCl3): δ 4.03 (s, 3H, -OCH3), 4.09 (s, 3H, -OCH3), 8.07 (dd, J = 6 Hz, 1H, H-3), 8.68 (s, 1H, H-5), 8.91 (d, 1H, H-2).13C NMR (75 MHz. CDCl3): δ 53.28 (-OCH3), 124.49 (C-5), 126.29 (C-3), 138.64 (C-4), 149.06 (C-6), 150.92 (C-2), 162.45 (C=O), 164.96 (C=O).

67-56-1 Synthesis

67-56-1
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499-80-9 Synthesis

499-80-9
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$8.00/1g

25658-36-0
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$45.00/50mg

Yield:25658-36-0 98%

Reaction Conditions:

with thionyl chloride for 5 h;Reflux;

Steps:

3.3 5.1.2.4 Preparation of dimethyl [2,2'-bipyridine]-4,4'-dicarboxylate (17)

General procedure: Thionyl chloride (300μL, 4.08mmol) was added to a suspension of 16 (400mg, 1.62mmol) in MeOH (30mL) in a dropwise fashion.
The mixture was heated at reflux temperature overnight.
Then, the solvent was removed under reduced pressure and the residue was partitioned between CH₂Cl₂ and water.
The organic layer was washed with saturated aqueous NaHCO₃ solution and dried over Na₂SO₄.
Filtration, evaporation in vacuo, and recrystallization in AcOEt gave 17 (400mg, 91%)

References:

Miyake, Yuka;Itoh, Yukihiro;Hatanaka, Atsushi;Suzuma, Yoshinori;Suzuki, Miki;Kodama, Hidehiko;Arai, Yoshinobu;Suzuki, Takayoshi [Bioorganic and Medicinal Chemistry,2019,vol. 27,# 6,p. 1119 - 1129]

499-80-9 Synthesis

499-80-9
297 suppliers
$8.00/1g

149-73-5 Synthesis