Potassium Carbonate → 3,5-Bis-(5-cyano-pyridin-2-yloxy)-benzoic Acid Ethyl Ester

HRID 1024711

Reaktionsgleichung

C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([OH:18])[CH:12]=1)[CH3:8].Cl[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1>CN(C=O)C>[CH2:7]([O:9][C:10](=[O:19])[C:11]1[CH:16]=[C:15]([O:17][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH:14]=[C:13]([O:18][C:21]2[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=2)[CH:12]=1)[CH3:8]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

Potassium carbonate 2.1 g (15.2 mmol) dissolved in DMF solution was added to 3,5-dihydroxy-benzoic acid ethyl ester 1.5 g (8.2 mmol) dissolved in 15 ml of DMF. This was followed by dropwise addition of 6-chloro-nicotinonitrile 2.1 g (15.2 mmol) dissolved in 5 ml of DMF. After complete addition, the reaction mixture was stirred at 60° C. for 8-10 h. The reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulphate and concentrated to afford a crude solid which was purified by column chromatography using hexane-ethyl acetate (10:2) to afford 2.5 g of the required product. 1H NMR (DMSO-d6): δ 1.30 (3H, t), 4.32 (2H, q), 7.35 (2H, d), 7.52 (1H, t), 7.68 (2H, d), 8.39 (2H, d), 8.69 (2H, s).

Aufarbeitung

additionAfter complete addition
customThe reaction mixture was quenched with ice cold water
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulphate
concentrationconcentrated
customto afford a crude solid which
customwas purified by column chromatography

Quellen und Nachweise

ORD-Eintrag: ord-e3f8d293e72b40c4b8e6f5c53e32f9d2
Quelldatensatz: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08722930B2

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