Hydrochloric Acid → HCID 86652839, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring suspension of 2-(1-methylethoxy)-4-{[5-(methylsulfonyl)pyridin-2-yl]oxy}aniline (32 g) in a mixture of acetonitrile (50 mL) and ethanol (100 mL) was added a concentrated hydrochloric acid (30 mL) at 0° C. After cooling to −5° C., a solution of sodium nitrite (8.2 g) in water (25 mL) was added dropwise to the mixture with keeping the temperature. below 0° C. The mixture was stirred at −10 to −5° C. for 30 min. The mixture was added to a mixture of ethyl 2-methyl-3-oxobutanoate (15.7 mL), potassium hydroxide (85%, 26 g), ethanol (140 mL) and water (140 mL) at −40 to −30° C. over 30 min. After stirring at −38° C. for 1 h, the resulting orange suspension was filtered to give the title compound as a wet orange solid. MS 434 (MH+).

Provenance & Evidence