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ChemicalBook CAS DataBase List 2-Ethoxybenzamide

2-Ethoxybenzamide synthesis

14synthesis methods
-

Yield: 98%

Reaction Conditions:

with [2,2]bipyridinyl;water;palladium diacetate in 1,4-dioxane at 90; for 24 h;Schlenk technique;Sealed tube;

Steps:

General Procedure XIII - Synthesis of Primary Amide Products in Water/Dioxane
General procedure: To an oven dried Schlenk carousel tube containing the appropriate nitrile (1 mmol) was added palladium acetate (11 mg, 5 mol%), 2,2'-bipyridine (7.8 mg, 5 mol%), dioxane (0.6 mL) and water (1.4 mL). The tube was then sealed and the reaction mixture heated at 70 °C (unless otherwise stated) for 24 hours. After being allowed to cool to room temperature, the reaction mixture was diluted with methanol (5 mL) and the solvent removed in vacuo on a rotary evaporator whilst azeotroping with toluene. Where the reaction had gone to quantitative conversion or the starting nitrile was volatile, the crude reaction mixture was passed through a short plug of silica to remove the catalyst (eluting with DCM/MeOH, 95:5). Otherwise, the primary amide products were purified by column chromatography (eluting with DCM/MeOH, 95:5, unless otherwise stated).

References:

Sanz Sharley, Daniel D.;Williams, Jonathan M.J. [Tetrahedron Letters,2017,vol. 58,# 43,p. 4090 - 4093] Location in patent:supporting information

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