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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 42070Erstellt: 25. Oktober 2026

Ethyl 2-aminobenzoate → Ethyl acetate hexane

https://huagongshe.com/reaction/42070

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthyl 2-aminobenzoateHCID 6877—
EduktBinap, (A+-)-HCID 634876—
EduktSodium t-butoxideHCID 23676156—
Edukt5-Bromo-2-(3-methoxyphenyl)pyridineHCID 49758519—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
ProduktEthyl acetate hexaneHCID 2122620698,4%
Produkt2-(6-(3-Methoxyphenyl)pyridin-3-ylamino)benzoic acidHCID 25186999—

Reaktionsbedingungen

Temperatur110 °C

Reaktionsschritte

In a schlenck tube, a mixture of 5-bromo-2-(3-methoxyphenyl)pyridine (Intermediate 27, 0.91 mmol, 0.23 g), ethyl 2-aminobenzoate (Intermediate 33, 0.91 mmol, 0.15 g), BINAP (0.05 mmol, 0.028 g), Pd2(dba)3 (0.05 mmol, 0.042 g) and NaOtBu (1.82 mmol, 0.175 g) in toluene (4 ml) was heated at 110° C. for 12 hours, under argon atmosphere. The solvent was evaporated and the solid residue was triturated with aqueous solution of 2N HCl and extracted with CHCl3. The crude mixture was purified by flash chromatography over SiO2 eluting with mixtures of hexane/ethyl acetate affording 0.078 g (yield 26%) of the expected compound.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08536165B2
Quelldatensatzuspto-grants-2013_09
ORD IDord-0c6010783c884be28f919b4217d37301
Quellennotizuspto-grants-2013_09