Hydrochloric Acid → HCID 76710730, compound

Participants

Reaction Steps

To a mixture of 2-methoxy-4-{[6-(methoxymethyl)pyridin-3-yl]oxy}aniline (20.1 g), ethanol (300 mL) and acetonitrile (30 mL) was added concentrated hydrochloric acid (14.2 mL) at 5° C. A solution of sodium nitrite (6.39 g) in water (20 mL) was added dropwise to the mixture at 5° C. The whole was stirred at room temperature for 30 min. The mixture was added to the mixture of potassium hydroxide (85%, 15.2 g), ethyl 2-methyl-3-oxobutanoate (12.2 g), ethanol (60 mL) and water (60 mL) at −20 to −10° C. over a period of 15 min. The whole was stirred at −20° C. for 30 min. Water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate:hexane=2:3 to 2:1, volume ratio) to give the title compound (12.58 g, 44%) as a brown oil. MS 374 (MH+).

Provenance & Evidence