Acetone, oxime → HCID 58928285, compound

Participants

Reaction Steps

Combine acetone oxime (3.1 g, 42.4 mmol) in dimethylformamide (15 mL) and add potassium t-butoxide (4.76 g, 42.4 mmol) and stir for 1 hour. Add (2-chloro-pyridin-3-yl)-(3-methoxy-phenyl)-methanone (8.40 g, 34 mmol) dissolved in dimethylformamide (10 mL) and stir at room temperature, overnight. Separate the product between water and ether and evaporate. Purify by column (silica) chromatography (10% ethyl acetate/dichloromethane) and then reflux in a mixture of 1:1 ethanol:5% aqueous hydrochloric acid. Work-up with 5% aqueous sodium hydroxide and ether and purify by flash chromatography (5% ethyl acetate in dichloromethane) to give the title compound (5.21 g, 68% Yield).

Provenance & Evidence